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The Tax Lawyer

The Tax Lawyer: Spring 2020

Recent Developments in Federal Income Taxation: The Year 2019

Bruce Alan McGovern, Cassady V Brewer, and James Delaney

Summary

  • This Article primarily focuses on subjects of broad general interest—tax accounting rules, determination of gross income, allowable deductions, treatment of capital gains and losses, corporate and partnership taxation, exempt organizations, and procedure and penalties.
  • This Article discusses the major administrative guidance issued in 2019, summarizes the 2019 legislative changes that, in our judgment, are the most important, and examines significant judicial decisions rendered in 2019.
  • Discussed legislation includes the the Taxpayer First Act, and the Further Consolidated Appropriations Act, 2020.
Recent Developments in Federal Income Taxation: The Year 2019
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Abstract

This Article summarizes and provides context to understand the most important developments in federal income taxation for the year 2019. The items discussed primarily consist of the following: (i) significant amendments to the Internal Revenue Code; (ii) important judicial decisions; and (iii) noteworthy administrative rulings and regulations promulgated by the Treasury Department and the Service. This Article primarily focuses on subjects of broad general interest—tax accounting rules, determination of gross income, allowable deductions, treatment of capital gains and losses, corporate and partnership taxation, exempt organizations, and procedure and penalties. This Article generally does not address items relating to federal estate and gift taxation, income taxation of trusts and estates, qualified pension and profitsharing plans, international taxation, or specialized industries such as banking, insurance, and financial services.

Introductory Notes

The year 2019 yielded many significant federal income tax developments. The Treasury Department and the Service continued to issue significant administrative guidance pursuant to the legislation Congress enacted in late 2017, “An Act to provide for reconciliation pursuant to titles II and V of the concurrent resolution on the budget for fiscal year 2018,” and colloquially known as the “2017 Tax Cuts and Jobs Act” (TCJA). Yet 2019 saw its own tax legislation. The “Taxpayer First Act,” enacted on July 1, 2019, directs certain organizational changes to the Service and makes several significant changes to procedural tax rules. The “Further Consolidated Appropriations Act, 2020,” enacted on December 20, 2019, repealed the taxes commonly known as the medical device tax and the Cadillac tax, modified the rules for contributions to and distributions from certain retirement plans, temporarily extended several expired or expiring provisions, and provided tax relief to those in areas affected by certain natural disasters. This Article discusses the major administrative guidance issued in 2019, summarizes the 2019 legislative changes that, in our judgment, are the most important, and examines significant judicial decisions rendered in 2019.

As a service to its readers, The Tax Lawyer anticipates publishing annual editions of these materials to provide tax practitioners, academics, and other professionals a comprehensive, yearly summary of the most important recent developments in federal income taxation.

I. Accounting

A. Accounting Methods

1. Many small businesses will not qualify for several simplifying provisions enacted in the TCJA, such as the use of the cash method of accounting, because they meet the definition of a “tax shelter.”

In a letter to the Service dated February 13, 2019, the American Institute of Certified Public Accountants brought to the attention of the Service the concern of many small businesses that, absent relief, they are ineligible for certain simplifying provisions enacted as part of the Tax Cuts and Jobs Act (TCJA) because the businesses meet the definition of a “tax shelter.” The letter requests appropriate relief.

Certain simplifying provisions enacted by the TCJA are available to businesses with average annual gross receipts not exceeding $25 million. The TJCA enacted several simplifying provisions that are available to a business if the business’s average annual gross receipts, measured over the three prior years, do not exceed $25 million. These include the following: (1) the ability of C corporations or partnerships with a C corporation as a partner to use the cash method of accounting (section 448(b)(3)), (2) the ability to use a method of accounting for inventories that either treats inventories as non-incidental materials and supplies or conforms to the taxpayer’s financial accounting treatment of inventories (section 471(c)(1)), (3) the ability to be excluded from applying the uniform capitalization rules of section 263A (section 263A(i)), (4) the small construction contract exception that permits certain taxpayers not to use the percentage-of-completion method of accounting for certain construction contracts (section 460(e)(1)(B)), and (5) the ability to be excluded from the section 163(j) limit on deducting business interest (section 163(j)(3)).

The simplifying provisions enacted by the TCJA generally are not available to a “tax shelter.” The simplifying provisions for small businesses listed above each state that they are not available to “a tax shelter prohibited from using the cash receipts and disbursements method of accounting under section 448(a)(3).” Section 448(a)(3) provides that a “tax shelter” cannot compute taxable income under the cash receipts and disbursements method of accounting, and according to section 448(d)(3), the term “tax shelter” for this purpose is defined in section 461(i)(3). Section 461(i)(3) defines the term “tax shelter” as “(A) any enterprise (other than a C corporation) if at any time interests in such enterprise have been offered for sale in any offering required to be registered with any Federal or State agency having the authority to regulate the offering of securities for sale, (B) any syndicate (within the meaning of section 1256(e)(3)(B)), and (C) any tax shelter (as defined in section 6662(d)(2)(C)(ii)).”

Many small businesses will meet the definition of a “syndicate” and therefore will be considered tax shelters. As discussed, the term “tax shelter” includes “any syndicate (within the meaning of section 1256(e)(3)(B)).” The term “syndicate,” according to section 1256(e)(3)(B), is “any partnership or other entity (other than a corporation which is not an S corporation) if more than 35% of the losses of such entity during the taxable year are allocable to limited partners or limited entrepreneurs.” Many small businesses will meet this definition and will be precluded from using the simplifying provisions enacted by the TCJA. Businesses that fluctuate between having income and having losses could be in the position of having to change accounting methods.

The AICPA has requested relief. The AICPA has asked the Service to exercise its authority, granted by section 1256(e)(3)(B), to treat an interest in an entity as not being held by a limited partner or a limited entrepreneur if certain conditions are met.

B. Inventories

There were no significant developments regarding this topic during 2019.

C. Installment Method

There were no significant developments regarding this topic during 2019.

D. Year of Inclusion or Deduction

1. Accrual-method taxpayers may have to recognize income sooner as a result of legislative changes.

Section 13221 of the TCJA amended section 451 to make two changes that affect the recognition of income and the treatment of advance payments by accrual-method taxpayers. Both changes apply to taxable years beginning after 2017. Any change in method of accounting required by these amendments for taxable years beginning after 2017 is treated as initiated by the taxpayer and made with the consent of the Service.

All events test linked to revenue recognition on certain financial statements. The legislation amended section 451 by redesignating section 451(b) through (i) as section 451(d) through (k) and adding a new section 451(b). New section 451(b) provides that, for accrual-method taxpayers, “the all events test with respect to any item of gross income (or portion thereof) shall not be treated as met any later than when such item (or portion thereof) is taken into account as revenue in” either (1) an applicable financial statement (AFS) or (2) another financial statement specified by the Service. Thus, taxpayers subject to this rule must include an item in income for tax purposes upon the earlier of satisfaction of the all events test or recognition of the revenue in an AFS (or other specified financial statement). According to the Conference Report that accompanied the legislation, this means, for example, that any unbilled receivables for partially performed services must be recognized to the extent the amounts are taken into income for financial statement purposes. Income from mortgage servicing contracts is not subject to the new rule. The new rule also does not apply to a taxpayer that does not have either an AFS or another specified financial statement.

An AFS is defined as (1) a financial statement that is certified as being prepared in accordance with generally accepted accounting principles that is (a) a 10-K or annual statement to shareholders required to be filed with the Securities and Exchange Commission, (b) an audited financial statement used for credit purposes, reporting to shareholders, partners, other proprietors, or beneficiaries, or for any other substantial nontax purpose, or (c) filed with any other federal agency for purposes other than federal tax purposes; (2) certain financial statements made on the basis of international financial reporting standards and filed with certain agencies of a foreign government; or (3) a financial statement filed with any other regulatory or governmental body specified by the Service.

Advance payments for goods or services. The legislation amended section 451 by redesignating section 451(b) through (i) as section 451(d) through (k) and adding a new section 451(c). This provision essentially codifies the deferral method of accounting for advance payments reflected in Revenue Procedure 2004-34. New section 451(c) provides that an accrual-method taxpayer who receives an advance payment can either (1) include the payment in gross income in the year of receipt or (2) elect to defer the category of advance payments to which such advance payment belongs. If a taxpayer makes the deferral election, then the taxpayer must include in gross income any portion of the advance payment required to be included by the AFS rule described above and include the balance of the payment in gross income in the taxable year following the year of receipt. An advance payment is any payment: (1) the full inclusion of which in gross income for the taxable year of receipt is a permissible method of accounting (determined without regard to this new rule), (2) any portion of which is included in revenue by the taxpayer for a subsequent taxable year in an AFS (as previously defined) or other financial statement specified by the Service, and (3) which is for goods, services, or such other items as the Service may identify. The term “advance payment” does not include several categories of items, including rent, insurance premiums, and payments with respect to financial instruments.

a. Guidance on accounting method changes relating to new section 451(b). Revenue Procedure 2018-60 modifies Revenue Procedure 2018-31 to provide procedures under section 446 and Regulation section 1.446-1(e) for obtaining automatic consent with respect to accounting method changes that comply with section 451(b), as amended by the TCJA. In addition, Revenue Procedure 2018-60 provides that for the first taxable year beginning after December 31, 2017, certain taxpayers are permitted to make a method change to comply with section 451(b) without filing a Form 3115, Application for Change in Accounting Method.

b. Proposed Regulations issued on requirement of section 451(b)(1) that an accrual-method taxpayer with an AFS treat the all events test as satisfied no later than the year in which it recognizes the revenue in an AFS. The Treasury Department and the Service have issued Proposed Regulations regarding the requirement of section 451(b)(1), as amended by the TCJA, that accrual-method taxpayers with an AFS must treat the all events test with respect to an item of gross income (or portion thereof) as met no later than when the item (or portion thereof) is taken into account as revenue in either an AFS or another financial statement specified by the Service (AFS income inclusion rule). New Proposed Regulation section 1.451-3 clarifies how the AFS income inclusion rule applies to accrual-method taxpayers with an AFS. Under Proposed Regulation section 1.451-3(d)(1), the AFS income inclusion rule applies only to taxpayers that have one or more AFSs covering the entire taxable year. In addition, the Proposed Regulations provide that the AFS income inclusion rule applies on a year-by-year basis, and therefore, an accrual-method taxpayer with an AFS in one taxable year that does not have an AFS in another taxable year must apply the AFS income inclusion rule in the taxable year for which it has an AFS but need not apply the rule in the taxable year for which it does not have an AFS. The Proposed Regulations clarify that the AFS income inclusion rule does not change the applicability of any exclusion provision, or the treatment of nonrecognition transactions, in the Code, regulations, or other published guidance.

Generally, the Proposed Regulations (1) clarify how the AFS inclusion rule applies to multi-year contracts, (2) describe and clarify the definition of an AFS for a group of entities, (3) define the meaning of the term “revenue” in an AFS, (4) define a transaction price and clarify how that price is to be allocated to separate performance obligations in a contract with multiple obligations, and (5) describe and clarify rules for transactions involving certain debt instruments.

The Regulations are proposed to apply generally to taxable years beginning on or after the date final regulations are published in the Federal Register. Because the tax treatment of certain fees (such as certain credit card fees), referred to as “specified fees,” is unclear, there is a one-year delayed effective date for Proposed Regulation section 1.451-3(i)(2), which applies to specified fees. Until final regulations are published, taxpayers can rely on the Proposed Regulations (other than the Proposed Regulations relating to specified fees) for taxable years beginning after December 31, 2017, provided that they (1) apply all the applicable rules contained in the Proposed Regulations (other than those applicable to specified fees) and (2) consistently apply the Proposed Regulations to all items of income during the taxable year (other than specified fees). Taxpayers can similarly rely, subject to the same conditions, on the Proposed Regulations with respect to specified credit card fees for taxable years beginning after December 31, 2018.

c. Proposed Regulations issued on advance payments for goods or services received by accrual-method taxpayers with or without an AFS. The Treasury Department and the Service have issued Proposed Regulations regarding accrual-method taxpayers with or without an AFS receiving advance payments for goods or services. The Proposed Regulations generally provide that an accrual-method taxpayer with an AFS includes an advance payment in gross income in the taxable year of receipt unless the taxpayer uses the deferral method in section 451(c)(1)(B) and Proposed Regulation section 1.451-8(c) (AFS deferral method). A taxpayer can use the AFS deferral method only if the taxpayer has an AFS, as defined in section 451(b)(1)(A)(i) or (ii). The term AFS is further defined in Proposed Regulation section 1.451-3(c)(1), issued on the same day as the Proposed Regulations. Under the AFS deferral method, a taxpayer with an AFS that receives an advance payment must include (1) the advance payment in income in the taxable year of receipt to the extent that it is included in revenue in its AFS and (2) the remaining amount of the advance payment in income in the next taxable year.

A similar deferral method is provided in Proposed Regulation section 1.451-8(d) for accrual-method taxpayers that do not have an AFS (non-AFS deferral method). Under the non-AFS deferral method, a taxpayer that receives an advanced payment must include (1) the advance payment in income in the taxable year of receipt to the extent that it is earned and (2) the remaining amount of the advance payment in income in the next taxable year. In Proposed Regulation section 1.451-8(b)(1)(i), the Proposed Regulations clarify that the definition of advance payment under the AFS and non-AFS deferral methods is consistent with the definition of an advance payment in Revenue Procedure 2004-34, which section 451(c) was meant to codify.

The Regulations are proposed to apply to taxable years beginning on or after the date the final regulations are published in the Federal Register. Until then, taxpayers can rely on the Proposed Regulations for taxable years beginning after December 31, 2017, provided that the taxpayer (1) applies all the applicable rules contained in the Proposed Regulations and (2) consistently applies the Proposed Regulations to all advance payments.

II. Business Income and Deductions

A. Income

1. What are a professional sports team’s player contracts really worth? Nothing, says the Service.

In Revenue Procedure 2019-18, the Service has provided a safe harbor for a professional sports team to treat certain personnel contracts (including those of players, managers, and coaches) and rights to draft players as having a zero value for purposes of determining gain or loss to be recognized for federal income tax purposes from the trade of a personnel contract or a draft pick. The Service provided this safe harbor in recognition of the fact that the value of professional sports personnel contracts fluctuates and is highly subjective. The safe harbor is designed to “avoid highly subjective, complex, lengthy, and expensive disputes between professional sports teams and the Service regarding the value of personnel contracts” and the resulting amount of gain or loss from their disposition. The Revenue Procedure applies to trades after April 10, 2019, but teams can choose to apply the Revenue Procedure to any open year.

To be eligible for the safe harbor, a professional sports team’s trade of personnel contracts and draft picks must meet four requirements: (1) all parties to the trade that are subject to federal income tax in the U.S. must treat the trade in a manner consistent with the Revenue Procedure, (2) each team that is a party to the trade must trade a personnel contract or a draft pick and no party to the trade may transfer property other than a personnel contract, draft pick, or cash, (3) no personnel contract or draft pick traded is an amortizable section 197 intangible, and (4) the financial statements of the teams that are parties to the trade do not reflect assets or liabilities resulting from the trade other than cash. If the safe harbor applies to a trade, then the following five principles govern the tax treatment of the trade:

  1. Gain or loss generally not recognized. Except to the extent required by the fifth principle (see below), a team making a trade within the safe harbor does not recognize gain or loss from the trade. (As described below, a team must recognize any gain or loss realized if it receives cash in the trade.)
  2. Only cash received is included in a team’s amount realized. A team that receives cash in a trade must include the cash in the amount realized. Because personnel contracts and draft picks are treated as having a value of zero, a team that receives only these assets has an amount realized of zero.
  3. A team’s basis in personnel contracts and draft picks received includes only cash provided. A team that provides cash in exchange for personnel contracts or draft picks has a basis in the assets acquired equal to the cash provided. A team that provides only personnel contracts or draft picks has a basis in the assets received of zero.
  4. Cash provided must be allocated equally to personnel contracts or draft picks received. A team that provides cash and receives more than one personnel contract or draft pick must determine its basis in the assets acquired by allocating the cash equally among the assets acquired.
  5. A team determines its gain or loss recognized by comparing its amount realized with the unrecovered basis of any personnel contracts and draft picks provided. A team making a trade within the safe harbor must recognize gain or loss to the extent its amount realized (as determined under the second principle) exceeds or falls below its unrecovered basis in the personnel contracts and draft picks it provides. The character of any gain or loss recognized is determined under the normal rules, e.g., a team’s gain or loss might be a section 1231 gain or loss and any gain a team recognizes might be ordinary under section 1245.

The Revenue Procedure provides the following four examples:

Example 1. Trade with no cash. In 2018, Team A trades Player Contract 1 to Team B for Player Contract 2. The teams apply the safe harbor in this revenue procedure. . . . [N]either Team A nor Team B has an amount realized or gain on the trade because neither team received cash in the trade. Team A has a $0 basis in Player Contract 2, and Team B has a $0 basis in Player Contract 1.
Example 2. One team provides cash in the trade. The facts are the same as in Example 1, except Team A trades Player Contract 1 and $10x to Team B for Player Contract 2. . . . Team A has no amount realized or gain on the trade because Team A did not receive cash in the trade. Team B has a $10x amount realized on the trade because Team B received $10x from Team A in the trade. . . . Team B must recognize $10x of gain, the excess of Team B’s $10x amount realized over its $0 basis in the Player Contract 2 it traded. Team B’s $10x gain is subject to the rules of §§ 1231 and 1245. . . . Team A has a $10x basis in Player Contract 2, the amount of cash Team A provided to Team B in the trade. Team A’s $10x basis is recovered through depreciation under § 1.167(a)-3(a) over the life of Player Contract 2. . . . Team B has a $0 basis in Player Contract 1 because Team B provided no cash to Team A in the trade.

Example 3. No cash in the trade, one team has unrecovered basis. (i) In 2019, Team C signs Player 3 to a contract (Player Contract 3) for 5 years. Under the terms of Player Contract 3, Team C pays Player 3 a $25x signing bonus in 2019. In each of 2019 and 2020, Team C takes a depreciation deduction under § 1.167(a)-3(a) of $5x for the $25x it paid to Player 3. In 2021, Team C trades Player Contract 3 to Team D for Player Contract 4, and the teams apply the safe harbor in this revenue procedure.

(ii) . . . [N]either Team C nor Team D has an amount realized or gain on the trade because neither team received cash in the trade. Because neither team provided cash in the trade, . . . each team has a $0 basis in the contract it received in the trade. . . . Team C may deduct in 2021 a $15x loss under §§ 165 and 1.167(a)-8, the excess of its unrecovered basis in Player Contract 3 over its amount realized of $0. Team C’s $15x loss is subject to the rules of § 1231.

Example 4. One team provides cash and one team has an unrecovered basis. The facts are the same as in Example 3, except Team D trades Player Contract 4 and $20x to Team C for Player Contract 3. . . . Team C has a $20x amount realized on the trade because Team C received $20x from Team D in the trade. . . . Team D has no amount realized or gain on the trade because Team D did not receive cash in the trade. Team C must recognize $5x of gain, the excess of Team C’s $20x amount realized over its $15x basis in the Player Contract 3 it traded. Team C’s $5x gain is subject to the rules of §§ 1231 and 1245. . . . Team C has a $0 basis in Player Contract 4 because Team C provided no cash to Team D in the trade. . . . Team D has a $20x basis in Player Contract 3, the amount of cash Team D provided to Team C in the trade. Team D’s $20x basis is recovered through depreciation under § 1.167(a)-3(a) over the life of Player Contract 3.

Example 5. Allocation of basis among multiple contracts. (i) In 2019, Team E trades Player Contract 5 and $30x to Team F for Player Contract 6, Player Contract 7, and Player Contract 8. The teams apply the safe harbor in this revenue procedure.

(ii) . . . Team E has no amount realized or gain on the trade because Team E did not receive cash in the trade. . . . Team E has a $30x basis in Player Contract 6, Player Contract 7, and Player Contract 8, collectively. . . . Team E has a basis of $10x in Player Contract 6, $10x in Player Contract 7, and $10x in Player Contract 8 because Team E allocates the $30x cash provided to Team F in the trade by dividing the basis equally among the three player contracts received in the trade. Team E’s $10x basis of each player contract is recovered through depreciation under § 1.167(a)-3(a) over the life of the respective player contract.

(iii) . . . Team F has a $30x amount realized on the trade because Team F received $30x from Team E in the trade. . . . Team F must recognize $30x of gain, the excess of Team F’s $30x amount realized over its $0 basis in the Player Contract 5 it traded. Team F’s $30x gain is subject to the rules of §§ 1231 and 1245. . . . Team F has a $0 basis in Player Contract 5 because Team F provided no cash to Team E in the trade.

B. Deductible Expenses versus Capitalization

There were no significant developments regarding this topic during 2019.

C. Reasonable Compensation

There were no significant developments regarding this topic during 2019.

D. Miscellaneous Deductions

1. Wrongful death settlement costs for the cocaine overdose death of the CEO’s girlfriend is not a deductible corporate business expense.

In Cavanaugh v. Commissioner, James Cavanaugh, the CEO and sole shareholder of Jani-King International, took a holiday trip to Cavanaugh’s villa in St. Maarten with his 27-year old girlfriend, a bodyguard, and a female Jani-King employee. Unfortunately, the girlfriend died from an overdose of cocaine. The girlfriend’s mother sued the individuals and the corporation for wrongful death. The taxpayer’s S corporation paid the full amount of the settlement, including a $250,000 reimbursement to Cavanaugh and claimed a business expense deduction.

The Tax Court (Judge Holmes) began its opinion in the case as follows:

Twenty-seven-year-old Colony Anne (Claire) Robinson left Texas in November 2002 for a Thanksgiving vacation in the Caribbean with her boyfriend, his bodyguard, and another employee of the company that he had spent decades building.

She did not return home alive.

The coroner’s report showed a massive amount of illegal drugs in her body and concluded that they were the likely cause of her death. Her mother sued the boyfriend and his company for wrongful death. The parties settled. The company paid most of the $2.3 million settlement directly; the boyfriend contributed $250,000, which the company then reimbursed. The company then claimed the entire $2.3 million as a deduction, along with nearly $180,000 in related legal fees.

The parties settled all of the issues in the case, but the Commissioner was unwilling to concede the deductibility of the settlement or the company’s reimbursement of Cavanaugh’s contribution.

Judge Holmes looked to the origin of the claim, which the court held to be applicable to the corporation’s payment in settlement of the wrongful death claim. Siding with the Service, the court concluded that, although the claim related to the conduct of the three corporate employees, the conduct was not related to the corporate business, i.e., its profit-seeking activities. The court also rejected the taxpayer’s theory that the bodyguard supplied cocaine in the course of his employment as a bodyguard and enabler for the CEO. Further, the court rejected the taxpayer’s argument that reimbursement of the taxpayer’s contribution to the settlement was contractually required under a corporate indemnity agreement. In addition, the court found that the payment was not deductible under the theory that it was made to protect the corporation’s business reputation because there was no evidence that underlay that theory.

Judge Holmes distinguished and refused to follow Kopp’s Co. v. United States, in which the Fourth Circuit upheld a corporation’s deduction for a payment made to settle pending litigation against the corporation brought by an individual injured by the CEO’s son who, while home on military leave and making “personal and permissive use of” a corporate-owned car, had an accident that severely injured the individual.

a. The corporation’s deductions are vaporized like freebase on appeal. In a per curiam opinion, the Court of Appeals for the Fifth Circuit affirmed the Tax Court’s decision. The court agreed with the Tax Court that under United States v. Gilmore the deductibility of the corporation’s litigation expenses is determined by the origin and character of the claim against it, and not by the claim’s potential consequences. The court rejected the taxpayer’s argument that the Gilmore analysis does not apply when the corporation itself is named as a defendant in the litigation that is settled. Decisions holding otherwise, the court stated, such as Kopp’s Co. v. United States “directly conflict with Gilmore, which is binding on this court.” In this case, the court reasoned, although the board of directors of Jani-King International approved the settlement on the advice of counsel, the claim arose from the provision of cocaine by employees of Jani-King, a non-business activity, and not from their employment by Jani-King. Accordingly, the court held that the Tax Court properly disallowed the corporation’s deduction of the settlement payment.

The court also held that the Tax Court properly had disallowed the corporation’s deduction of its reimbursement of Cavanaugh for the $250,000 he had contributed. According to the court, Cavanaugh had waived the argument that the reimbursement was required by the corporation’s by-laws, and the payment was a nondeductible voluntary payment by the corporation of another’s legal expenses.

2. Rats! We knew that we should have been architects or engineers instead of tax advisers.

Section 11011 of the TCJA added section 199A, thereby creating an unprecedented, new deduction for trade or business (and certain other) income earned by sole proprietors, partners of partnerships (including members of LLCs taxed as partnerships or as sole proprietorships), and shareholders of S corporations. Section 101 of the Consolidated Appropriations Act, 2018 (CAA 2018), signed by the President on March 23, 2018, amended section 199A principally to address issues related to agricultural or horticultural cooperatives. New section 199A is intended to put owners of flow-through entities (but also including sole proprietorships) on par with C corporations that will benefit from the new reduced 21% corporate tax rate; however, in our view, the new provision actually makes many flow-through businesses even more tax-favored than they were under pre-TCJA law.

Big Picture. Oversimplifying a bit to preserve our readers’ (and the authors’) sanity, new section 199A essentially grants a special 20% deduction for “qualified business income” (principally, trade or business income, but not wages) of certain taxpayers (but not most personal service providers except those falling below an income threshold). In effect, then, new section 199A reduces the top marginal rate of certain taxpayers with respect to their trade or business income (but not wages) by 20% (i.e., the maximum 37% rate becomes 29.6% on qualifying business income assuming the taxpayer is not excluded from the benefits of the new statute). Most high-earning (over $415,000 taxable income if married filing jointly) professional service providers (including lawyers, accountants, investment advisers, physicians, etc., but not architects or engineers) are excluded from the benefits of new section 199A. Of course, the actual operation of new section 199A is considerably more complicated, but the highlights (lowlights?) are as summarized above.

Effective dates. Section 199A applies to taxable years beginning after 2017 and before 2026.

Initial Observations. Our initial, high-level observations of new section 199A are set forth below:

How section 199A applies. New section 199A is applied at the individual level of any qualifying taxpayer by first requiring a calculation of taxable income excluding the deduction allowed by section 199A and then allowing a special deduction of 20% of qualified business income against taxable income to determine a taxpayer’s ultimate federal income tax liability. Thus, the deduction is not an above-the-line deduction allowed in determining adjusted gross income; it is a deduction that reduces taxable income. The deduction is available both to those who itemize deductions and those who take the standard deduction. The deduction cannot exceed the amount of the taxpayer’s taxable income reduced by net capital gain. The section 199A deduction applies for income tax purposes; it does not reduce self-employment taxes. Query what those states that piggyback off federal taxable income will do with respect to new section 199A. Presumably, the deduction will be disallowed for state income tax purposes.

Eligible taxpayers. Section 199A(a) provides that the deduction is available to “a taxpayer other than a corporation.” The deduction of section 199A is available to individuals, estates, and trusts. For S corporation shareholders and partners, the deduction applies at the shareholder or partner level. Section 199A(f)(4) directs the Treasury Department to issue regulations that address the application of section 199A to tiered entities.

Qualified trades or businesses (or, what’s so special about architects and engineers?)—section 199A(d). One component of the section 199A deduction is 20% of the taxpayer’s qualified business income. To have qualified business income, the taxpayer must be engaged in a qualified trade or business, which is defined as any trade or business other than (1) the trade or business of performing services as an employee or (2) a specified service trade or business. A specified service trade or business is defined (by reference to section 1202(e)(3)(A)) as “any trade or business involving the performance of services in the fields of health, . . . law, accounting, actuarial science, performing arts, consulting, athletics, financial services, brokerage services, or any trade or business where the principal asset of such trade or business is the reputation or skill of 1 or more of its employees.” Architects and engineers must be special, because they are included under section 1202(e)(3)(A) but are specifically excluded from the definition of a specified service trade or business. There is no reasoned explanation for this exclusion in the 2017 TCJA Conference Report.

Note: Taxpayers whose taxable income, determined without regard to the section 199A deduction, is below a specified threshold are not subject to the exclusion for specified service trades or businesses, i.e., these taxpayers can take the section 199A deduction even if they are doctors, lawyers, accountants, etc. The thresholds are $315,000 for married taxpayers filing jointly and $157,500 for all other taxpayers. (These figures will be adjusted for inflation in years beginning after 2018.) Taxpayers whose taxable income exceeds these thresholds are subject to a phased reduction of the benefit of the section 199A deduction until taxable income reaches $415,000 for joint filers and $207,500 for all other taxpayers, at which point the service business cannot be treated as a qualified trade or business.

Qualified business income—section 199A(c). One component of the section 199A deduction is 20% of the taxpayer’s qualified business income, which is generally defined as the net amount from a qualified trade or business of items of income, gain, deduction, and loss included or allowed in determining taxable income. Excluded from the definition are: (1) income not effectively connected with the conduct of a trade or business in the United States, (2) specified investment-related items of income, gain, deduction, or loss, (3) amounts paid to an S corporation shareholder that are reasonable compensation, (4) guaranteed payments to a partner for services, (5) to the extent provided in regulations, payments to a partner for services rendered other than in the partner’s capacity as a partner, and (6) qualified REIT dividends or qualified publicly traded partnership income (because these two categories are separate components of the section 199A deduction).

Determination of the amount of the section 199A deduction—section 199A(a)–(b). Given the much-touted simplification thrust of the TCJA, determining the amount of a taxpayer’s section 199A deduction is surprisingly complex. One way to approach the calculation is to think of the section 199A deduction as the sum of two buckets, subject to one limitation. Bucket 1 is the sum of the following from all of the taxpayer’s qualified trades or businesses, determined separately for each qualified trade or business: the lesser of (1) 20% of the qualified trade or business income with respect to the trade or business or (2) the greater of (a) 50% of the W-2 wages with respect to the qualified trade or business or (b) the sum of 25% of the W-2 wages with respect to the qualified trade or business plus 2.5% of the unadjusted basis immediately after acquisition of all qualified property. Bucket 2 is 20% of the sum of the taxpayer’s qualified REIT dividends and qualified publicly traded partnership income. The limitation is that the sum of Buckets 1 and 2 cannot exceed the amount of the taxpayer’s taxable income reduced by the taxpayer’s net capital gain. Thus, a taxpayer’s section 199A deduction is determined by adding together Buckets 1 and 2 and applying the limitation.

Note: The W-2 wages and capital limitation does not apply to taxpayers whose taxable income is below the $157,500/$315,000 thresholds mentioned earlier in connection with the definition of a qualified trade or business. For taxpayers below the thresholds, Bucket 1 is simply 20% of the qualified trade or business income. For taxpayers above the thresholds, the wage and capital limitation phases in and fully applies once taxable income reaches $207,500/$415,000.

Revised rules for cooperatives and their patrons. Section 101 of the CCA, 2018 amended section 199A to fix what was commonly referred to as the “grain glitch.” Under section 199A as originally enacted, farmers selling goods to agricultural cooperatives were permitted to claim a deduction effectively equal to 20% of gross sales, while farmers selling goods to independent buyers effectively could claim a deduction equal to 20% of net income. Some independent buyers argued that this difference created an unintended market preference for producers to sell to agricultural cooperatives. Under the amended version of section 199A, agricultural cooperatives determine their deduction under rules set forth in section 199A(g) that are similar to those in old (and now repealed) section 199. The section 199A deduction of an agricultural cooperative is equal to nine percent of the lesser of (1) the cooperative’s qualified production activities income or (2) taxable income calculated without regard to specified items. The cooperative’s section 199A deduction cannot exceed 50% of the W-2 wages paid by the cooperative. A cooperative can pass its section 199A deduction through to their farmer patrons. In addition, the legislation modified the original version of section 199A to eliminate the 20% deduction for qualified cooperative dividends received by a taxpayer other than a corporation. Instead, under the amended statute, taxpayers are entitled to a deduction equal to the lesser of 20% of net income recognized from agricultural and horticultural commodity sales or their overall taxable income, subject to a wage and capital limitation.

An incentive for business profits rather than wages. Given a choice, most taxpayers who qualify for the section 199A deduction would prefer to be compensated as an independent contractor (i.e., 1099 contractor) rather than as an employee (i.e., W-2 wages), unless employer-provided benefits dictate otherwise because, to the extent such compensation is “qualified business income,” a taxpayer may benefit from the 20% deduction authorized by section 199A.

The “Edwards/Gingrich loophole” for S corporations becomes more attractive. New section 199A exacerbates the games currently played by S corporation shareholders regarding minimizing compensation income (salaries and bonuses) and maximizing residual income from the operations of the S corporation. For qualifying S corporation shareholders, minimizing compensation income will not only save on the Medicare portion of payroll taxes, but also maximize any deduction available under new section 199A.

a. Let the games begin! Treasury and the Service have issued final Regulations under section 199A. The Treasury Department and the Service have finalized Proposed Regulations under section 199A. The Regulations address the following six general areas. In addition, Regulation section 1.643(f)-1 provides anti-avoidance rules for multiple trusts.

Operational rules. Regulation section 1.199A-1 provides guidance on the determination of the section 199A deduction. The operational rules define certain key terms, including qualified business income, qualified REIT dividends, qualified publicly traded partnership income, specified service trade or business, and W-2 wages. According to Regulation section 1.199A-1(b)(14), a “trade or business” is “a trade or business that is a trade or business under section 162 (a section 162 trade or business) other than performing services as an employee.” In addition, if tangible or intangible property is rented or licensed to a trade or business conducted by an individual or a “relevant passthrough entity” (a partnership or S corporation owned directly or indirectly by at least one individual, estate, or trust) that is commonly controlled (within the meaning of Regulation section 1.199A-1(b)(1)(i)), then the rental or licensing activity is treated as a trade or business for purposes of section 199A even if the rental or licensing activity would not, on its own, rise to the level of a trade or business.

The operational rules also provide guidance on the computation of the section 199A deduction for those with taxable income below and above the $157,500/$315,000 thresholds mentioned earlier, as well as rules for determining the carryover of negative amounts of qualified business income and negative amounts of combined qualified REIT dividends and qualified publicly traded partnership income. The Regulations clarify that, if a taxpayer has an overall loss from combined qualified REIT dividends and qualified publicly traded partnership income, the overall loss does not affect the amount of the taxpayer’s qualified business income and instead is carried forward separately to offset qualified REIT dividends and qualified publicly traded partnership income in the succeeding year. The operational rules also provide rules that apply in certain special situations, such as Regulation section 1.199A-1(e)(1), which clarifies that the section 199A deduction has no effect on the adjusted basis of a partner’s partnership interest or the adjusted basis of an S corporation shareholder’s stock basis.

Determination of W-2 Wages and the Unadjusted Basis of Property. Regulation section 1.199A-2 provides rules for determining the amount of W-2 wages and the unadjusted basis immediately after acquisition (UBIA) of qualified property. The amount of W-2 wages and the UBIA of qualified property are relevant to taxpayers whose taxable incomes exceed the $157,500/$315,000 thresholds mentioned earlier. For taxpayers with taxable income in excess of these limits, one component of their section 199A deduction (Bucket 1 described earlier) is the lesser of (1) 20% of the qualified trade or business income with respect to the trade or business or (2) the greater of (a) 50% of the W-2 wages with respect to the qualified trade or business or (b) the sum of 25% of the W-2 wages with respect to the qualified trade or business plus 2.5% of the UBIA of all qualified property. The rules of Regulation section 1.199A-2 regarding W-2 wages generally follow the rules under former section 199 (the now-repealed domestic production activities deduction) but, unlike the rules under former section 199, the W-2 wage limitation in section 199A applies separately for each trade or business.

The amount of W-2 wages allocable to each trade or business generally is determined according to the amount of deductions for those wages allocated to each trade or business. Wages must be “properly allocable” to qualified business income to be taken into account for purposes of section 199A, which means that the associated wage expense must be taken into account in determining qualified business income. In the case of partnerships and S corporations, a partner or S corporation shareholder’s allocable share of wages must be determined in the same manner as that person’s share of wage expenses. The Regulations provide special rules for the application of the W-2 wage limitation to situations in which a taxpayer acquires or disposes of a trade or business. Simultaneously with the issuance of the Regulations, the Service issued Revenue Procedure 2019-11, which provides guidance on methods for calculating W-2 wages for purposes of section 199A.

The Regulations also provide guidance on determining the UBIA of qualified property. Regulation section 1.199A-2(c)(1) restates the statutory definition of qualified property, which is depreciable tangible property that is (1) held by, and available for use in, a trade or business at the close of the taxable year, (2) used in the production of qualified business income, and (3) for which the depreciable period has not ended before the close of the taxable year. The Regulations clarify that UBIA is determined without regard to both depreciation and amounts that a taxpayer elects to treat as an expense (e.g., pursuant to section 179, 179B, or 179C) and that UBIA is determined as of the date the property is placed in service. Special rules address property transferred with a principal purpose of increasing the section 199A deduction, like-kind exchanges under section 1031, involuntary conversions under section 1033, subsequent improvements to qualified property, and allocation of UBIA among partners and S corporation shareholders.

Qualified Business Income, Qualified REIT Dividends, and Qualified Publicly Traded Partnership Income. Regulation section 1.199A-3 provides guidance on the determination of the components of the section 199A deduction: qualified business income (QBI), qualified REIT dividends, and qualified publicly traded partnership income. The Proposed Regulations generally restate the statutory definitions of these terms.

Among other significant rules, the Regulations clarify that (1) gain or loss treated as ordinary income under section 751 is considered attributable to the trade or business conducted by the partnership and therefore can be QBI if the other requirements of section 199A are satisfied, (2) section 1231 gain or loss is not QBI if the section 1231 “hotchpot” analysis results in these items becoming long-term capital gains and losses, and that section 1231 gain or loss is QBI if the section 1231 analysis results in these items becoming ordinary (assuming all other requirements of section 199A are met), (3) losses previously suspended under sections 465, 469, 704(d), or 1366(d) that are allowed in the current year are treated as items attributable to the trade or business in the current year, except that such losses carried over from taxable years ending before January 1, 2018, are not taken into account in a later year for purposes of computing QBI, and (4) net operating losses carried over from prior years are not taken into account in determining QBI for the current year, except that losses disallowed in a prior year by section 461(l) (the provision enacted by the TCJA that denies excess business losses for noncorporate taxpayers) are taken into account in determining QBI for the current year.

Aggregation Rules. Regulation section 1.199A-4 permits, but does not require, taxpayers to aggregate trades or businesses for purposes of determining the section 199A deduction if the requirements in Regulation section 1.199A-4(b)(1) are satisfied. The Treasury Department and the Service declined to adopt the existing aggregation rules in Regulation section 1.469-4 that apply for purposes of the passive activity loss rules on the basis that those rules, which apply to “activities” rather than trades or businesses and which serve purposes somewhat different from those of section 199A, are inappropriate. Instead, the Regulations permit aggregation if the following five requirements are met: (1) the same person, or group of persons, directly or indirectly owns 50% or more of each of the businesses to be aggregated, (2) the required level of ownership exists for the majority of the taxable year in which the items attributable to the trade or business are included in income, (3) all of the items attributable to each trade or business to be aggregated are reported on returns with the same taxable year (not taking into account short taxable years), (4) none of the aggregated businesses is a specified service trade or business, and (5) the trades or businesses to be aggregated meet at least two of three factors designed to demonstrate that the businesses really are part of a larger, integrated trade or business. The Regulations also impose a consistency rule under which an individual who aggregates trades or businesses must consistently report the aggregated trades or businesses in subsequent taxable years. In addition, the Regulations require that taxpayers attach to the relevant return a disclosure statement that identifies the trades or businesses that are aggregated.

Specified Service Trade or Business. Regulation section 1.199A-5 provides extensive guidance on the meaning of the term “specified service trade or business.” For purposes of section 199A, a qualified trade or business is any trade or business other than (1) the trade or business of performing services as an employee or (2) a specified service trade or business. Section 199A(d)(2) defines a specified service trade or business (by reference to section 1202(e)(3)(A)) as “any trade or business involving the performance of services in the fields of health, . . . law, accounting, actuarial science, performing arts, consulting, athletics, financial services, brokerage services, or any trade or business where the principal asset of such trade or business is the reputation or skill of 1 or more of its employees.” Architects and engineers are excluded. For taxpayers whose taxable incomes are below the $157,500/$315,000 thresholds mentioned earlier, a business is a qualified trade or business even if it is a specified service trade or business.

The Regulations provide guidance on what it means to be considered as providing services in each of the referenced categories. Regarding the last category, the Regulations state that a trade or business in which the principal asset is the reputation or skill of one or more employees means any trade or business that consists of one or more of the following: (1) a trade or business in which a person receives fees, compensation, or other income for endorsing products or services, (2) a trade or business in which a person licenses or receives fees (or other income) for use of an individual’s image, likeness, name, signature, voice, trademark, or symbols associated with that person’s identity, or (3) receiving fees or other income for appearing at an event or on radio, television, or another media format. The Regulations set forth several examples. The Regulations also create a de minimis rule under which a trade or business (determined before application of the aggregation rules) is not a specified service trade or business if (1) it has gross receipts of $25 million or less and less than ten percent of its gross receipts is attributable to the performance of services in a specified service trade or business or (2) it has more than $25 million in gross receipts and less than five percent of its gross receipts is attributable to the performance of services in a specified service trade or business.

Special Rules for Passthrough Entities, Publicly Traded Partnerships, Trusts, and Estates. Regulation section 1.199-6 provides guidance necessary for passthrough entities, publicly traded partnerships, trusts, and estates to determine the section 199A deduction of the entity or its owners. The Regulations provide computational steps for passthrough entities and publicly traded partnerships and special rules for applying section 199A to trusts and decedents’ estates.

Effective Dates. The Regulations generally apply to taxable years ending after February 8, 2019, the date on which the final Regulations were published in the Federal Register. Nevertheless, taxpayers can rely on the final Regulations in their entirety or on the Proposed Regulations published in the Federal Register on August 16, 2018, in their entirety, for taxable years ending in 2018. However, to prevent abuse, certain provisions of the Regulations apply to taxable years ending after December 22, 2017, the date of enactment of the TCJA. In addition, Regulation section 1.643(f)-1, which provides anti-avoidance rules for multiple trusts, applies to taxable years ending after August 16, 2018.

b. The Service has issued a Revenue Procedure that provides guidance on methods for calculating W-2 wages for purposes of section 199A. Revenue Procedure 2019-11 provides three methods for calculating “W-2 wages” as that term is defined in section 199A(b)(4) and Regulation section 1.199A-2. The first method (the unmodified Box method) allows for a simplified calculation while the second and third methods (the modified Box 1 method and the tracking wages method) provide greater accuracy. The methods are substantially similar to the methods provided in Revenue Procedure 2006-47, which applied for purposes of former section 199. The Revenue Procedure applies to taxable years ending after December 31, 2017.

c. The Service has provided a safe harbor under which a rental real estate enterprise will be treated as a trade or business solely for purposes of section 199A. Whether a rental real estate activity constitutes a trade or business for federal tax purposes has long been an area of uncertainty, and the significance of this uncertainty has been heightened by Congress’s enactment of section 199A. To help mitigate this uncertainty, the Service has issued Revenue Procedure 2019-38 to provide a safe harbor under which a rental real estate enterprise will be treated as a trade or business solely for purposes of section 199A and the Regulations issued under that provision. If a rental real estate enterprise does not fall within the safe harbor, it can still be treated as a trade or business if it otherwise meets the definition of a trade or business in Regulation section 1.199A-1(b)(14).

The Revenue Procedure defines a “rental real estate enterprise” as “an interest in real property held for the production of rents [that] may consist of an interest in a single property or interests in multiple properties.” Those relying on the Revenue Procedure must hold the interest directly or through a disregarded entity and must either treat each property held for the production of rents as a separate enterprise or treat all similar properties held for the production of rents (with certain exceptions) as a single enterprise. Commercial and residential real estate cannot be part of the same enterprise. Taxpayers that choose to treat similar properties as a single enterprise must continue to do so (including with respect to newly acquired similar properties) when the taxpayer continues to rely on the safe harbor, but a taxpayer that treats similar properties as separate enterprises can choose to treat similar properties as a single enterprise in future years.

For a rental real estate enterprise to fall within the safe harbor, the following four requirements must be met:

  1. Separate books and records are maintained to reflect income and expenses for each rental real estate enterprise;
  2. For rental real estate enterprises that have been in existence fewer than four years, 250 or more hours of rental services are performed per year with respect to the rental enterprise. For rental real estate enterprises that have been in existence for at least four years, in any three of the five consecutive taxable years that end with the taxable year, 250 or more hours of rental services are performed per year with respect to the rental real estate enterprise;
  3. The taxpayer maintains contemporaneous records, including time reports, logs, or similar documents, regarding the following: (i) hours of all services performed, (ii) description of all services performed, (iii) dates on which such services were performed, and (iv) who performed the services. If services with respect to the rental real estate enterprise are performed by employees or independent contractors, the taxpayer may provide a description of the rental services performed by such employee or independent contractor, the amount of time such employee or independent contractor generally spent performing such services for the enterprise, and time, wage, or payment records for such employee or independent contractor. Such records are to be made available for inspection at the request of the Service. The contemporaneous records requirement does not apply to taxable years beginning prior to January 1, 2020; and
  4. The taxpayer attaches to a timely filed original return (or an amended return in the case of 2018 only) a statement that describes the properties included in each enterprise, describes rental real estate properties acquired and disposed of during the taxable year, and represents that the requirements of the Revenue Procedure are satisfied.

The Revenue Procedure also provides a definition of “rental services.”

The Revenue Procedure applies to taxable years ending after December 31, 2017. For 2018, taxpayers can rely on the safe harbor in the Revenue Procedure or the one in the proposed Revenue Procedure that was set forth in Notice 2019-7.

3. Tax Court holds that, although a struggling business owner never used two properties in his trade or business, mortgage interest paid with respect to the properties was not subject to limitations on investment interest and was deductible on Schedule C.

In Pugh v. Commissioner, the taxpayer, who holds a Bachelor of Science degree in electrical engineering, operated a sole proprietorship, Pi Integrated Systems (Pi), which was engaged in software development. Pi operated from an office in the taxpayer’s home. He borrowed money to purchase two vacant lots in 2005 and 2006 and paid interest on the loans. He purchased two steel buildings, disassembled them, and stored some of the components on one of the properties. He planned to reassemble the buildings on the vacant lots, as reflected in a site plan prepared by an architect in 2007 and to use the buildings as the headquarters of Pi. Pi experienced the loss of a major customer, a loss of revenue, and a loss of employees, and the plans to reassemble the buildings never took place. As of the date of trial in 2017, the lots remained vacant and some of the building components had been sold for scrap metal.

On his federal income tax returns for 2010 and 2011, which were submitted to the Service long after they were due and apparently never processed by the Service, the taxpayer claimed several deductions on Schedule C, including a deduction for the mortgage interest paid on the loans used to finance the acquisition of the vacant lots and a deduction for legal fees. The Service allowed all but a small amount of the legal fees as deductions but disallowed the deductions for mortgage interest. The Service argued that, because the properties were never actually used in the taxpayer’s trade or business, the interest was not deductible as it was either “personal interest” within the meaning of section 163(h) or was “investment interest” within the meaning of section 163(d) and, therefore, deductible only to the extent of net investment income, which the taxpayer did not have.

The Tax Court (Judge Carluzzo) first concluded that the interest paid by the taxpayer was not “investment interest,” which is defined in section 163(d)(3)(A) as deductible interest paid or accrued on indebtedness properly allocable to property held for investment. The term “property held for investment” is defined in section 163(d)(5)(A) as property that produces income of a type described in section 469(e)(1), which generally describes passive investment income such as interest, dividends, rents, and royalties. According to the court, the land the taxpayer purchased was not property held for investment, and therefore the interest he paid on the loans used to finance the purchase could not be investment interest. The Tax Court also held that the interest was not nondeductible “personal interest” as defined in section 163(h)(2) because it fit into one of the categories excluded from the definition of personal interest. One of those categories, set forth in section 163(h)(2)(A), is interest paid or accrued on indebtedness properly allocable to a trade or business (other than the trade or business of performing services as an employee). The Tax Court concluded that “the properties were not actually used in petitioner’s trade or business during the years in issue. Nevertheless, we are satisfied that the properties were certainly ‘allocable’ to that business.”

The Tax Court disallowed the taxpayer’s deduction of the small amount of remaining legal fees that the Service had not allowed. “Because [the taxpayer] has failed to establish the nature of the legal services involved, how those services relate to his trade or business, or the amounts actually paid or incurred for those services, he is not entitled to a deduction for legal fees in excess of the amount already allowed by [the Service] for each year in issue.”

4. A retroactive incentive to make commercial buildings energy efficient.

Section 130 of the Taxpayer Certainty and Disaster Tax Relief Act of 2019 retroactively extended the section 179D deduction for the cost of energy efficient commercial building property. Generally, these are improvements designed to reduce energy and power costs with respect to the interior lighting systems, heating, cooling, ventilation, and hot water systems of a commercial building by 50% or more in comparison to certain standards. The lifetime limit on deductions under section 179D is $1.80 per square foot. This provision had expired for property placed in service after December 31, 2017. As extended, the deduction is available for property placed in service before January 1, 2021.

5. Standard mileage rates for 2020.

In Notice 2020-5, the Service reduced slightly the standard mileage rate for business miles in 2019 to 57.5 cents per mile (from 58.0 cents in 2019) and the medical/moving rate to 17 cents per mile (from 20 cents in 2019). The charitable mileage rate remains fixed by section 170(i) at 14 cents. The portion of the business standard mileage rate treated as depreciation went up to 27 cents per mile for 2020 (from 26 cents in 2019). The maximum standard automobile cost may not exceed $50,400 (unchanged from 2019) for passenger automobiles (including trucks and vans) for purposes of computing the allowance under a fixed and variable rate plan.

The Notice reminds taxpayers that (1) the business standard mileage rate cannot be used to claim an itemized deduction for unreimbursed employee travel expenses because, in the TCJA, Congress disallowed miscellaneous itemized deductions for 2020 and (2) the standard mileage rate for moving has limited applicability for the use of an automobile as part of a move during 2020 because, in the TCJA, Congress disallowed the deduction of moving expenses for 2020 (except for members of the military on active duty who move pursuant to military orders incident to a permanent change of station, who can still use the standard mileage rate for moving).

6. Dazed and confused. The Tax Court has held that section 280E is not a penalty provision and therefore does not violate the Eighth Amendment’s prohibition on excessive fines.

In Northern California Small Business Assistants, Inc. v. Commissioner, the Service disallowed the deductions of the taxpayer, a corporation that operated a medical marijuana dispensary, under section 280E. Section 280E disallows any deduction or credit otherwise allowable if such amount is paid or incurred in connection with a trade or business “if such trade or business (or the activities which comprise such trade or business) consists of trafficking in controlled substances . . . .” The taxpayer challenged the disallowance and moved for summary judgment on the grounds that section 280E (1) imposes a gross receipts tax as a penalty in violation of the Eighth Amendment to the U.S. Constitution, (2) disallows only ordinary and necessary business expenses otherwise deductible under section 162 and does not disallow items deductible under other Code provisions, and (3) does not apply to marijuana businesses that operate legally under state law.

In a reviewed opinion (10–2–3) by Judge Goeke with which Judges Thornton, Marvel, Paris, Kerrigan, Buch, Lauber, Nega, Pugh, and Ashford agreed, the Tax Court rejected all three arguments and denied the taxpayer’s motion for summary judgment. The Eighth Amendment provides that “[e]xcessive bail shall not be required, nor excessive fines imposed, nor cruel and unusual punishments inflicted.” The court observed that, to conclude that section 280E violates the Excessive Fines Clause of the Eighth Amendment, it would have to conclude that the Eighth Amendment applies to corporations, that section 280E operates as a penalty, and that the penalty in this case is excessive. On the issue of whether section 280E is a penalty provision, the court reasoned that Congress has the power to lay and collect taxes under Article I, Section 8 of the Constitution and has the power under the Sixteenth Amendment to lay and collect taxes on “incomes, from whatever source derived.” The court further reasoned that deductions are a matter of legislative grace and that it is “unquestionable” that Congress has the power under the Sixteenth Amendment to tax gross income. Section 280E, the court stated, “is directly tied to Congress’ policy objective to limit and deter trafficking in illegal controlled substances” and “is not simply an attempt by Congress to punish violators of State law with no legitimate Federal objective.” In the court’s view, “[t]here is simply no way to reconcile the argument that section 280E creates a penalty with the authority of Congress to tax gross income.” Because the court concluded that section 280E is not a penalty provision, it declined to address whether the Eighth Amendment applies to corporations (an issue left open by the Supreme Court in Browning-Ferris Industries of Vermont, Inc. v. Kelco Disposal, Inc.) or whether the penalty in this case was excessive.

The court also rejected the taxpayer’s argument that section 280E disallows only business expenses otherwise deductible under section 162 and not other deductions such as taxes deductible under section 164 or depreciation deductible under section 167. The court reasoned that both the language of section 280E, which provides that “[n]o deduction or credit shall be allowed,” and the broader statutory scheme are inconsistent with the taxpayer’s position. Finally, the court rejected the taxpayer’s argument that section 280E, which applies to trades or businesses that consist of trafficking in controlled substances, does not apply to businesses that operate legally under state law. The court had rejected this same argument in previous decisions.

Concurring opinion by Judge Lauber. Judge Lauber concurred separately to respond to a partial dissent by Judge Copeland. Judge Lauber emphasized that the fact that Congress enacted section 280E to deter trafficking in controlled substances “does not make the sanction a ‘fine’ or ‘punishment’ within the meaning of the Eighth Amendment.” According to Judge Lauber, taking into account Congress’s power to tax gross income, “[t]here is no plausible authority for the proposition that section 280E ‘punishes’ taxpayers, within the meaning of the Eighth Amendment, by denying deductions for business expenses.” Judges Marvel, Ashford, and Goeke agreed with Judge Lauber.

Concurring opinion by Judge Morrison. Judge Morrison, joined by Judge Foley, concurred in the result only. Judge Morrison declined to advance a view on whether section 280E is a fine and instead would have denied the taxpayer’s motion for summary judgment on the ground that, even if section 280E were a fine, the taxpayer had not shown that it was excessive as applied to the taxpayer.

Partial dissenting opinion by Judge Gustafson. Judge Gustafson, joined by Judge Copeland and in part by Judge Goeke, concurred in the result on the ground that the taxpayer’s motion for summary judgment did not show that there was a genuine dispute regarding whether the penalty at issue was excessive. Judge Gustafson dissented from the court’s conclusion that section 280E is not a penalty for purposes of the Eighth Amendment. First, Judge Gustafson argued that Congress can constitutionally tax only “income,” and that taxing gross receipts without allowance of deductions for expenses incurred to produce the income is not a tax on “income.”

Congress taxes something other than a taxpayer’s “income” when it taxes gross receipts without accounting for basis or COGS—and, I would hold, when it taxes gross receipts without accounting for the ordinary and necessary expenses that are incurred in the course of business and must be paid before one can be said to have gain.

Section 280E, according to Judge Gustafson, taxes something other than “income” and violates the Sixteenth Amendment.

Next, Judge Gustafson argued that, even if section 280E does not violate the Sixteenth Amendment, the majority had erred in reasoning that, because Congress can disallow deductions pursuant to its powers under the Sixteenth Amendment, section 280E necessarily does not violate the Eighth Amendment. He reasoned that, if Congress granted a tax exemption to organizations of one religion but not another or allowed deductions only to individuals of one sex, and if a taxpayer challenged congressional action as a violation of the First or Fifth Amendment, “it would widely miss the mark to dismiss his complaint with the maxim that deductions are a matter of ‘legislative grace’ under the Sixteenth Amendment.”

Finally, Judge Gustafson argued that, even if deductions are a matter of legislative grace, “the application of section 280E results in the imposition of a ‘fine’ for purposes of the Eighth Amendment’s excessive fines clause.” He rejected as unpersuasive the opinion of the Court of Appeals for the Tenth Circuit in Alpenglow Botanicals, LLC v. United States, the only federal appellate decision to consider (and reject) the argument that section 280E violates the Eighth Amendment. That opinion is unpersuasive, he argued,

because the Court of Appeals for the Tenth Circuit never performed an Eighth Amendment constitutional analysis suited to that case but relied instead on an inapposite authority in reaching its conclusion that section 280E does not impose a penalty.

In Judge Gustafson’s view, further proceedings were required to address whether the Eighth Amendment applies to corporations and whether the penalty that results from section 280E is excessive.

Partial dissenting opinion by Judge Copeland. Judge Copeland, joined by Judges Gale and Gustafson, concurred in the result on the ground that, assuming section 280E imposes a penalty, the taxpayer’s motion for summary judgment did not provide evidence of excessiveness. Like Judge Gustafson, Judge Copeland dissented from the court’s conclusion that section 280E is not a penalty for purposes of the Eighth Amendment. She argued that section 280E is punitive in both its operation, which disallows all otherwise allowable deductions rather than a narrow range of expenses, and its purpose, which is “to deter the sale of controlled substances to penalize the drug trade, as the legislative history explicitly states.” Judge Copeland did not express a view on whether the Eighth Amendment applies to corporations.

E. Depreciation & Amortization

1. Certain depreciation and amortization provisions of the TCJA:

a. Increased limits and expansion of eligible property under section 179. Section 13101 of the TCJA increased the maximum amount a taxpayer can deduct under section 179 to $1 million (increased from $520,000). This limit is reduced dollar-for-dollar to the extent the taxpayer puts an amount of section 179 property in service that exceeds a specified threshold. The legislation increased this threshold to $2.5 million (increased from $2,070,000). These changes apply to property placed in service in taxable years beginning after 2017. The legislation did not change the limit on a taxpayer’s section 179 deduction for a sport utility vehicle, which remains at $25,000. The basic limit of $1 million, the phase-out threshold of $2.5 million, and the sport utility vehicle limitation of $25,000 all will be adjusted for inflation for taxable years beginning after 2018.

Revised and expanded definition of qualified real property. Section 13101 of the TCJA also simplified and expanded the definition of “qualified real property,” the cost of which can be deducted under section 179 (subject to the applicable limits just discussed). Prior to amendment by the TCJA, section 179(f) defined qualified real property as including “qualified leasehold improvement property,” “qualified restaurant property,” and “qualified retail improvement property.” The legislation revised the definition of qualified real property by replacing these three specific categories with a single category, “qualified improvement property” as defined in section 168(e)(6). Section 168(e)(6) defines qualified improvement property (subject to certain exceptions) as “any improvement to an interior portion of a building which is nonresidential real property if such improvement is placed in service after the date such building was first placed in service.” In addition, the legislation expanded the category of qualified real property by defining it to include the following improvements to nonresidential real property placed in service after the date the property was first placed in service: (1) roofs, (2) heating, ventilation, and air-conditioning property, (3) fire protection and alarm systems, and (4) security systems. These changes apply to property placed in service in taxable years beginning after 2017.

Section 179 property expanded to include certain personal property used to furnish lodging. Section 13101 of the TCJA also amended section 179(d)(1). The effect of this amendment was to include within the definition of section 179 property certain depreciable tangible personal property used predominantly to furnish lodging or in connection with furnishing lodging (such as beds or other furniture, refrigerators, ranges, and other equipment).

Guidance on the procedure for electing to treat qualified real property as section 179 property. In Revenue Procedure 2019-8, the Service provided the procedure by which taxpayers can elect to deduct the cost of qualified real property under section 179(a). According to the Revenue Procedure, for qualified real property placed in service in taxable years beginning after 2017, taxpayers make the election “by filing an original or amended Federal tax return for that taxable year in accordance with procedures similar to those in section 1.179-5(c)(2) and section 3.02 of Revenue Procedure 2017-33.” Taxpayers that have filed an original return can elect to increase the portion of the cost of qualified real property deducted under section 179(a) by filing an amended return and will not be treated as having revoked a prior election under section 179 for that year.

b. Goodbye, basis; hello 100% section 168(k) bonus first-year depreciation! Section 13201 of the TCJA amended section 168(k)(1) and 168(k)(6) to permit taxpayers to deduct 100% of the cost of qualified property for the year in which the property is placed in service. This change applies to property acquired and placed in service after September 27, 2017, and before 2023. The percentage of the property’s adjusted basis that can be deducted is reduced from 100% to 80% in 2023, 60% in 2024, 40% in 2025, and 20% in 2026. (These periods are extended by one year for certain aircraft and certain property with longer production periods.) Property acquired on or before September 27, 2017, and placed in service after that date is eligible for bonus depreciation of 50% if placed in service before 2018, 40% if placed in service in 2018, 30% if placed in service in 2019, and is ineligible for bonus depreciation if placed in service after 2019.

Used property eligible for bonus depreciation. The legislation also amended section 168(k)(2)(A) and (E) to make used property eligible for bonus depreciation under section 168(k). Prior to this change, property was eligible for bonus depreciation only if the original use of the property commenced with the taxpayer. This new rule applies to property acquired and placed in service after September 27, 2017. Note, however, that used property is eligible for bonus depreciation only if it is acquired “by purchase” as defined in section 179(d)(2). This means that used property is not eligible for bonus depreciation if the property is (1) acquired from certain related parties (within the meaning of sections 267 or 707(b)), (2) acquired by one component member of a controlled group from another component member of the same controlled group, (3) property the basis of which is determined by reference to the basis of the same property in the hands of the person from whom it was acquired (such as a gift), or (4) property the basis of which is determined under section 1014 (relating to property acquired from a decedent). In addition, property acquired in a like-kind exchange is not eligible for bonus depreciation.

Qualified property. The definition of “qualified property” eligible for bonus depreciation continues to include certain trees, vines, and plants that bear fruits or nuts (deductible at a 100% level for items planted or grafted after September 27, 2017, and before 2023, and at reduced percentages for items planted or grafted after 2022 and before 2027). The definition also includes a qualified film or television production. Excluded from the definition is any property used in a trade or business that has had floor plan financing indebtedness (unless the business is exempted from the section 163(j) interest limitation because its average annual gross receipts over a three-year period do not exceed $25 million).

Section 280F $8,000 increase in first-year depreciation. For passenger automobiles that qualify, section 168(k)(2)(F) increases by $8,000 in the first year the section 280F limitation on the amount of depreciation deductions allowed. The legislation continues this $8,000 increase for passenger automobiles acquired and placed in service after 2017 and before 2023. For passenger automobiles acquired on or before September 27, 2017, and placed in service after that date, the previously scheduled phase-down of the $8,000 increase applies as follows: $6,400 if placed in service in 2018, $4,800 if placed in service in 2019, and $0 after 2019.

c. Changes to the 280F depreciation limits on passenger automobiles and removal of computer and peripheral equipment from the definition of listed property. Section 13202 of the TCJA amended section 280F(a)(1)(A) to increase the maximum amount of allowable depreciation for passenger automobiles and for which bonus depreciation under section 168(k) is not claimed. The maximum amount of allowable depreciation is $10,000 for the year in which the vehicle is placed in service, $16,000 for the second year, $9,600 for the third year, and $5,760 for the fourth and later years in the recovery period. The legislation also amended section 280F(d)(4) to remove computer or peripheral equipment from the definition of listed property. Both changes apply to property placed in service after 2017 in taxable years ending after 2017.

d. Changes to the depreciation of certain property used in a farming business. Section 13203 of the TCJA made two changes with respect to the depreciation of any machinery or equipment (other than any grain bin, cotton ginning asset, fence, or other land improvement) that is used in a farming business. For this purpose, the term “farming business” is defined in section 263A(e)(4). The legislation amended section 168(b)(2) and (e)(3)(B) to repeal the required use of the 150% declining balance method and to reduce the recovery period from seven years to five years. Accordingly, such machinery and equipment should be depreciable over five years using the double-declining balance method and the half-year convention. This change applies to property placed in service after 2017 in taxable years ending after 2017.

Mandatory use of ADS for farming businesses that elect out of the new interest limitation. Section 13205 of the TCJA amended section 168 to add new section 168(g)(1)(G), which requires a farming business that elects out of the newly-enacted interest limitation of section 163(j) to use the alternative depreciation system for any property with a recovery period of ten years or more. This change applies to taxable years beginning after 2017.

Note: Aside from longer recovery periods, the requirement to use the alternative depreciation system for property with a recovery period of ten years or more would seem to have the effect of making such property ineligible for bonus depreciation under section 168(k) even if it normally would be eligible for bonus depreciation.

e. Revised definitions and minor adjustments to recovery periods for real property. With respect to real property, section 13204 of the TCJA amended section 168 to simplify certain definitions and make minor adjustments for purposes of the alternative depreciation system.

Three categories consolidated into one. The legislation replaced the categories of “qualified leasehold improvement property,” “qualified restaurant property,” and “qualified retail improvement property” with a single category, “qualified improvement property.” Section 168(e)(6) defines qualified improvement property (subject to certain exceptions) as “any improvement to an interior portion of a building which is nonresidential real property if such improvement is placed in service after the date such building was first placed in service.” Qualified improvement property is depreciable over 15 years using the straight-line method and is subject to the half-year convention. This change applies to property placed in service after 2017.

Note: The Conference Agreement indicates that the normal recovery period for qualified improvement property is 15 years, but section 168 as amended does not reflect this change. This should be addressed in technical corrections.

Residential rental property has a 30-year ADS recovery period. Section 13204 of the TCJA also reduced the recovery period for residential rental property for purposes of the alternative depreciation system from 40 years to 30 years. The general recovery period for such property remains at 27.5 years. This change applies to property placed in service after 2017. An optional depreciation table for residential rental property with a 30-year ADS recovery period appears in Revenue Procedure 2019-8.

Mandatory use of ADS for real property trades or businesses electing out of the new interest limitation. Finally, section 13204 of the TCJA amended section 168 to add new section 168(g)(1)(F) and (g)(8), which require a real property trade or business that elects out of the newly-enacted interest limitation of section 163(j) to use the alternative depreciation system for nonresidential real property, residential rental property, and qualified improvement property. This change applies to taxable years beginning after 2017.

Note: Aside from longer recovery periods, the requirement to use the alternative depreciation system for qualified improvement property would seem to have the effect of making qualified improvement property ineligible for bonus depreciation under section 168(k).

f. The Service has issued final Regulations that provide guidance on section 168(k) first-year depreciation. The Treasury Department and the Service have finalized, with some changes, Proposed Regulations issued under section 168(k). These Regulations provide guidance regarding the additional first-year depreciation deduction (so-called “bonus depreciation”) under section 168(k) as amended by the TCJA. They affect taxpayers who deduct depreciation for qualified property acquired and placed in service after September 27, 2017. Generally, the Regulations provide detailed guidance on the requirements that must be met, including specific requirements that apply to used property, for depreciable property to qualify for the additional first-year depreciation deduction provided by section 168(k).

The Preamble to the final Regulations notes that some comments submitted on the Proposed Regulations had requested that the final Regulations provide that “qualified improvement property” (discussed above) placed in service after 2017 is eligible for additional first-year depreciation under section 168(k). The Treasury Department and the Service declined to adopt this suggested change because the relevant statutory provisions do not permit it. Although the Conference Agreement that accompanied the TCJA stated that qualified improvement property is depreciable over 15 years, section 168 as amended by the TCJA does not reflect this change. Accordingly, the recovery period for qualified improvement property is 39 years. Because property that qualifies for the additional first-year depreciation deduction generally must have a recovery period of 20 years or less, qualified improvement property placed in service after 2017 is not eligible for bonus depreciation.

The final Regulations are effective on September 24, 2019, but taxpayers can choose to apply them in their entirely to qualified property acquired and placed in service (or planted or grafted) after September 27, 2017, during taxable years ending on or after September 28, 2017. For qualified property acquired and placed in service (or planted or grafted) after September 27, 2017, during taxable years ending after that date and before September 24, 2019, taxpayers can rely on the Proposed Regulations.

2. The Service comes to the rescue to allow depreciation of passenger automobiles that qualify for 100% bonus depreciation under section 168(k).

Under section 280F(a)(1)(B)(i), the “unrecovered basis” of a passenger automobile that is subject to the section 280F limits on depreciation is treated as an expense for the first taxable year after the automobile’s recovery period. For passenger automobiles eligible for 100% first-year depreciation under section 168(k), the amount by which the cost of the vehicle (before any section 179 deduction) exceeds the first-year section 280F limitation is the “unrecovered basis” for purposes of section 280F(a)(1)(B)(i). In other words, if a taxpayer does not elect out of 100% first-year bonus depreciation, then the taxpayer can deduct in the year the vehicle is placed in service the maximum amount allowed under section 280F(a)(1)(A) and then cannot deduct any additional portion of the vehicle’s cost until after the recovery period has passed, at which point the taxpayer can deduct the unrecovered cost as an expense, subject to the annual $5,670 limitation specified in section 280F(a)(1)(B)(ii).

Revenue Procedure 2019-13 gives the following example of this situation:

For example, if a calendar-year taxpayer places in service in December 2018 a passenger automobile that costs $50,000 and is qualified property for which the 100-percent additional first-year depreciation deduction is allowable, the 100-percent additional first-year depreciation deduction and any section 179 deduction for this property is limited to $18,000 under section 280F(a)(1)(A)(i) (see Table 2 of Rev. Proc. 2018-25) and the excess amount of $32,000 is recovered by the taxpayer beginning in 2024, subject to the annual limitation of $5,760 under section 280F(a)(1)(B)(ii).

To avoid this result, the Revenue Procedure provides a safe-harbor method of accounting for determining depreciation deductions for passenger automobiles that qualify for 100% bonus depreciation under section 168(k). The safe-harbor method permits taxpayers to deduct a portion of the vehicle’s cost in each year of the recovery period. The Service issued a similar ruling in response to Congress’s enactment of 100% bonus depreciation for 2010.

Bonus Depreciation Under Section 168(k) as Amended by the TCJA. Section 13201 of the TCJA amended section 168(k)(1) and 168(k)(6) to permit taxpayers to deduct 100% of the cost of qualified property for the year in which the property is placed in service. This change applies to property acquired and placed in service after September 27, 2017, and before 2023. The percentage of the property’s adjusted basis that can be deducted is reduced from 100% to 80% in 2023, 60% in 2024, 40% in 2025, and 20% in 2026. (These periods are extended by one year for certain aircraft and certain property with longer production periods.) Property acquired before September 28, 2017 and placed in service on or after that date is eligible for bonus depreciation of 50% if placed in service before 2018, 40% if placed in service in 2018, 30% if placed in service in 2019, and is ineligible for bonus depreciation if placed in service after 2019. The legislation also amended section 168(k)(2)(A) and (E) to make used property eligible for bonus depreciation under section 168(k).

Section 280F $8,000 increase in first-year depreciation. For passenger automobiles that qualify, section 168(k)(2)(F) increases by $8,000 in the first year the section 280F limitation on the amount of depreciation deductions allowed. The TCJA continues this $8,000 increase for passenger automobiles acquired and placed in service after September 27, 2017, and before 2023. (For passenger automobiles acquired before September 28, 2017, and placed in service on or after that date, the previously scheduled phase-down of the $8,000 increase applies as follows: $6,400 if placed in service in 2018, $4,800 if placed in service in 2019, and $0 after 2019.)

According to Revenue Procedure 2018-25, the section 280F depreciation limits for business use of small vehicles placed in service during 2018 are as follows:

Passenger Automobiles acquired before 9/28/17 and placed in serviceduring 2018 with section 168(k) first-year recovery:

1st Tax Year

$16,400

2nd Tax Year

$16,000

3rd Tax Year

$ 9,600

Each Succeeding Year

$ 5,760

Passenger Automobiles acquired after 9/27/17 and placed in serviceduring 2018 with section 168(k) first-year recovery:

1st Tax Year

$18,000

2nd Tax Year

$16,000

3rd Tax Year

$ 9,600

Each Succeeding Year

$ 5,760

Passenger Automobiles placed in service during 2018 with no section168(k) first-year recovery: 

1st Tax Year

$10,000

2nd Tax Year

$16,000

3rd Tax Year

$ 9,600

Each Succeeding Year

$ 5,760

Safe Harbor of Revenue Procedure 2019-13. Revenue Procedure 2019-13 provides a safe-harbor method of accounting for determining depreciation deductions for passenger automobiles (other than leased vehicles) that are acquired after September 27, 2017, qualify for 100% bonus depreciation under section 168(k), have a cost (before any section 179 deduction) that exceeds the first-year section 280F limitation, and for which the taxpayer does not elect to take a section 179 deduction. A taxpayer adopts this safe-harbor method by applying it on its federal tax return for the first taxable year succeeding the year in which a passenger automobile is placed in service.

To use the safe harbor, a taxpayer must (1) use the appropriate optional depreciation table (available in Publication 946) to calculate depreciation deductions for the passenger automobile, (2) deduct the section 280F first-year limitation amount in the year the vehicle is placed in service (a figure published annually by the Service), (3) calculate depreciation for the passenger automobile for each succeeding taxable year in the recovery period by multiplying the remaining adjusted depreciable basis (the vehicle’s cost before any section 179 deduction less the section 280F first-year limitation amount) by the percentage specified in the appropriate optional depreciation table, subject to the section 280F limitation amounts, and (4) deduct any remaining basis of the vehicle in the first taxable year succeeding the end of the recovery period, subject to the limitation of section 280F(a)(1)(B)(ii) ($5,760 in the tables above) and carrying forward any excess to the succeeding taxable year to deduct in a similar manner. If section 280F(b) applies to the vehicle) (i.e., it is not predominantly used in a qualified business use), then the safe harbor ceases to apply in the first taxable year in which section 280F(b) applies. The Revenue Procedure is effective on February 13, 2019.

Examples. Revenue Procedure 2019-13 provides the following examples.

Example 1—Application of section 280F(a) safe harbor method of accounting. In 2018, X, a calendar-year taxpayer, purchased and placed in service for use in its business a new passenger automobile that costs $60,000. The passenger automobile is 5-year property under section 168(e), is qualified property under section 168(k) for which the 100-percent additional first-year depreciation deduction is allowable, and is used 100 percent in X’s trade or business. X does not claim a section 179 deduction for the passenger automobile and does not make an election under section 168(b), (g)(7), or (k). X depreciates the passenger automobile under the general depreciation system by using the 200-percent declining balance method, a 5-year recovery period, and the half-year convention. X adopts the safe harbor method of accounting provided in section 4.03 of this revenue procedure. As a result:

(a) X must use the applicable optional depreciation table that corresponds with the 200-percent declining balance method of depreciation, a 5-year recovery period, and the half-year convention, for determining the depreciation deductions for the passenger automobile (see Table A-1 in Appendix A of Publication 946);

(b) For 2018, X deducts depreciation of $18,000 for the passenger automobile, which is the depreciation limitation for 2018 under section 280F(a)(1)(A)(i) (see Table 2 in Revenue Procedure 2018-25). As a result, the remaining adjusted depreciable basis of the passenger automobile as of January 1, 2019, is $42,000 ($60,000 unadjusted depreciable basis less $18,000 depreciation deduction claimed for 2018);

(c) For 2019 through 2023, the total depreciation allowable for the passenger automobile for each taxable year is determined by multiplying the annual depreciation rate in the applicable optional depreciation table by the remaining adjusted depreciable basis of $42,000, subject to the limitation under section 280F(a)(1)(A) for that year. Accordingly, for 2019, the total depreciation allowable for the passenger automobile is $13,440 (32 percent multiplied by the remaining adjusted depreciable basis of $42,000). Because this amount is less than the depreciation limitation of $16,000 for 2019 (see Table 2 in Revenue Procedure 2018-25), X deducts $13,440 as depreciation on its federal income tax return for the 2019 taxable year. For 2020, the total depreciation allowable for the passenger automobile is $8,064 (19.20 percent multiplied by $42,000). Because this amount is less than the depreciation limitation of $9,600 for 2020 (see Table 2 in Revenue Procedure 2018-25), X deducts $8,064 as depreciation on its federal income tax return for the 2020 taxable year. Below is a table showing the depreciation allowable for the passenger automobile under the safe harbor method of accounting for the 2018 through 2023 taxable years. X deducts these amounts.

Taxable Year Depreciation limitations under Table 2 of Rev. Proc. 2018-25  Depreciation deduction under the safe harbor
2018 $18,000 $18,000
2019 $16,000  $13,440 ($42,000 x .32)
2020 $9,600  $ 8,064 ($42,000 x .1920)
2021 $5,760  $ 4,838 ($42,000 x .1152)
2022 $5,760  $ 4,838 ($42,000 x .1152)
2023 $5,760 $ 2,419 ($42,000 x .0576)
TOTAL    $51,599

(d) As of January 1, 2024 (the beginning of the first taxable year succeeding the end of the recovery period), the adjusted depreciable basis of the passenger automobile is $8,401 ($60,000 unadjusted depreciable basis less the total depreciation allowable of $51,599 for 2018-2023 (see above table)). Accordingly, for the 2024 taxable year, X deducts depreciation of $5,760 for the passenger automobile (the lesser of the adjusted depreciable basis of $8,401 as of January 1, 2024, or the section 280F(a)(1)(B)(ii) limitation of $5,760).

(e) As of January 1, 2025, the adjusted depreciable basis of the passenger automobile is $2,641 ($8,401 adjusted depreciable basis as of January 1, 2024, less the depreciation claimed of $5,760 for 2024). Accordingly, for the 2025 taxable year, X deducts depreciation of $2,641 for the passenger automobile (the lesser of the adjusted depreciable basis of $2,641 as of January 1, 2025, or the section 280F(a)(1)(B)(ii) limitation of $5,760).

Example 2—Section 179 deduction claimed. The facts are the same as in Example 1, except X elects to treat $18,000 of the cost of the passenger automobile as an expense under section 179. As a result, this passenger automobile is not within the scope of this revenue procedure pursuant to section 3.01(4) of this revenue procedure. Accordingly, the safe harbor method of accounting in section 4.03 of this revenue procedure does not apply to the passenger automobile. For 2018, the 100-percent additional first-year depreciation deduction and the section 179 deduction for this passenger automobile is limited to $18,000 under section 280F(a)(1)(A)(i) (see Table 2 of Revenue Procedure 2018-25). Therefore, for 2018, X deducts $18,000 for the passenger automobile under section 179, and X deducts the excess amount of $42,000 beginning in 2024, subject to the annual limitation of $5,760 under section 280F(a)(1)(B)(ii).
Example 3—Section 168(k)(7) election made. The facts are the same as in Example 1, except X makes an election under section 168(k)(7) to not claim the 100-percent additional first-year depreciation deduction for 5-year property placed in service during 2018. As a result, the 100-percent additional first-year depreciation deduction is not allowable for the passenger automobile. Accordingly, the passenger automobile is not within the scope of this revenue procedure pursuant to section 3.01(2) of this revenue procedure, and the safe harbor method of accounting in section 4.03 of this revenue procedure does not apply to the passenger automobile. For 2018 and subsequent taxable years, X determines the depreciation deductions for the passenger automobile in accordance with the general depreciation system of section 168(a), subject to the section 280F(a) limitations.

3. We suppose it makes sense that racehorses have a swift recovery period.

Section 114 of the Taxpayer Certainty and Disaster Tax Relief Act of 2019 retroactively extended the section 168(e)(3)(A)(i) classification of racehorses as three-year MACRS property so that the classification applies to racehorses placed in service before January 1, 2021. A racehorse placed in service after December 31, 2020, qualifies for the three-year recovery period only if it is more than two years old when placed in service. This provision allowing classification of all racehorses as three-year property regardless of age had expired for racehorses placed in service after December 31, 2017.

4. Good news for those who placed motorsports entertainment complexes in service during 2018 and 2019 or who will do so in 2020.

Section 115 of the Taxpayer Certainty and Disaster Tax Relief Act of 2019 retroactively extended the section 168(e)(3)(C)(ii) classification of motorsports entertainment complexes as seven-year property to include property placed in service through December 31, 2020. Such property is depreciable over a seven-year recovery period using the straight-line method. This provision had expired for property placed in service after December 31, 2017.

F. Credits

1. A three-year credit for small employers that implement automatic contribution arrangements.

Section 105 of the Setting Every Community Up for Retirement Enhancement Act of 2019 (SECURE Act) added new section 45T, which provides a $500 credit to certain small employers that implement an eligible automatic contribution arrangement (as defined in section 414(w)(3)) in a qualified employer plan (as defined in section 4972(d)). Generally, an automatic contribution arrangement allows an employer automatically to deduct elective deferrals from an employee’s wages unless the employee makes an election not to contribute or to contribute a different amount. The credit is available for each of three years to an “eligible employer,” which is defined in section 408(p)(2)(C)(i) as an employer that has 100 or fewer employees who received at least $5,000 of compensation from the employer for the preceding year. An eligible employer can include the credit among the credits that are components of the general business credit under section 38(b). New section 45T applies to taxable years beginning after December 31, 2019.

2. Congress gives a “thumbs up” to new energy efficient homes.

Section 129 of the Taxpayer Certainty and Disaster Tax Relief Act of 2019 retroactively extended the section 45L credit of $2,000 or $1,000 (depending on the projected level of fuel consumption) an eligible contractor can claim for each qualified new energy-efficient home constructed by the contractor and acquired by a person from the contractor for use as a residence during the tax year. As extended, the credit is available for homes acquired before January 1, 2021. This provision had expired for homes acquired after December 31, 2017.

3. Congress has extended through 2020 the credit for employers that pay wages to certain employees during periods of family and medical leave.

Section 142 of the Taxpayer Certainty and Disaster Tax Relief Act of 2019 extended section 45S, which was enacted as part of the TCJA, through December 31, 2020. Section 45S provides that an “eligible employer” can include the “paid family and medical leave credit” among the credits that are components of the general business credit under section 38(b). The credit is equal to a percentage of the amount of wages paid to “qualifying employees” during periods in which the employees are on family and medical leave. The credit is available against both the regular tax and the alternative minimum tax.

Amount of the credit. To be eligible for the credit, the employer must pay during the period of leave at a rate that is at least 50% of the wages normally paid to the employee. The credit is 12.5% of the wages paid, increased by 0.25 percentage points for each percentage point by which the rate of payment exceeds 50%. The maximum credit is 25% of wages. Thus, if an employer pays an employee at a rate that is 60% of the employee’s normal wages, the credit is 15% of wages paid (12.5% plus 2.5 percentage points). The credit reaches 25% when the employer pays at a rate that is 100% of the employee’s normal wages. The credit cannot exceed the amount derived from multiplying the employee’s normal hourly rate by the number of hours for which the employee takes leave. The compensation of salaried employees is to be prorated to an hourly wage under regulations to be issued by the Treasury Department. The maximum amount of leave for any employee that can be taken into account for purposes of the credit is 12 weeks per taxable year.

Eligible employer. An eligible employer is defined as one who has in place a written policy that (1) allows all full-time “qualifying employees” not less than two weeks of annual paid family and medical leave and that allows all part-time qualifying employees a commensurate amount of leave on a pro rata basis and (2) requires that the rate of payment under the program is not less than 50% of the wages normally paid to the employee.

Eligible employee. An eligible employee is defined as any employee as defined in section 3(e) of the Fair Labor Standards Act of 1938 who has been employed by the employer for one year or more and who, for the preceding year, had compensation not in excess of 60% of the compensation threshold for highly compensated employees. For 2019, the threshold for highly compensated employees (see section 414(q)(1)(B)) was $125,000. Thus, for purposes of determining the credit in 2020, an employee is an eligible employee only if his or her compensation for 2019 did not exceed $75,000 ($125,000 x 60%).

Family and medical leave. The term “family and medical leave” is defined as leave described under sections 102(a)(1)(a)–(e) or 102(a)(3) of the Family and Medical Leave Act of 1993. (Generally, these provisions describe leave provided because of the birth or adoption of a child, a serious health condition of the employee or certain family members, or the need to care for a service member with a serious injury or illness.) If an employer provides paid leave as vacation leave, personal leave, or other medical or sick leave, this paid leave is not considered to be family and medical leave.

No double benefit. Pursuant to section 280C(a), no deduction is allowed for the portion of wages paid to an employee for which this new credit is taken. Thus, if an employer pays $10,000 to an employee and takes a credit for 25%, or $2,500, the employer may deduct as a business expense only $7,500 of the wages.

Effective date. The credit is available for wages paid in taxable years beginning after December 31, 2017, and before January 1, 2021.

4. Employers who retained employees despite becoming inoperable in areas affected by qualified disasters are eligible for a 40% employee retention credit.

Section 203 of the Taxpayer Certainty and Disaster Tax Relief Act of 2019 provides that an “eligible employer” can include “the 2018 through 2019 qualified disaster employee retention credit” among the credits that are components of the general business credit under section 38(b). The credit is equal to 40% of “qualified wages” for each “eligible employee.” The cap on the amount of qualified wages of an employee that can be taken into account is $6,000 (reduced by the amount of qualified wages with respect to the employee that may be taken into account for any prior taxable year). Thus, the maximum credit per employee is $2,400.

An “eligible employer” is an employer that conducted an active trade or business in a qualified disaster zone at any time during the incident period of the relevant qualified disaster, if the trade or business became inoperable at any time during the period beginning on the first day of the incident period of the qualified disaster and ending on December 20, 2019 (the date of enactment) as a result of damage sustained by reason of such qualified disaster. An “eligible employee” is an employee whose principal place of employment with an eligible employer, determined immediately before the relevant qualified disaster, was in the disaster zone of that qualified disaster.

The term “qualified wages” means wages (as defined in section 51(c)(1), but without regard to section 3306(b)(2)(B)) paid or incurred by an eligible employer with respect to an eligible employee during the period beginning on the date the trade or business first became inoperable at the employee’s principal place of employment and ending on the earlier of (1) the date on which the trade or business resumed significant operations at the principal place of employment or (2) the date that is 150 days after the last day of the incident period of the relevant qualified disaster. Wages can be qualified wages regardless of whether the employee performed no services, performed services at a different location, or performed services at the employee’s principal place of employment before significant operations resumed. An employee is not considered an eligible employee if the employer is allowed a credit with respect to the employee under section 51(a), i.e., an eligible employer cannot claim the 40% credit with respect to an employee for any period if the employer is allowed a Work Opportunity Tax Credit with respect to the employee under section 51 for that period.

Several key terms are defined in section 201 of the Taxpayer Certainty and Disaster Tax Relief Act of 2019. These are as follows:

  1. The term “incident period” with respect to any qualified disaster is the period specified by FEMA as the period during which the disaster occurred, except that the period cannot be treated as beginning before January 1, 2018, or ending after January 19, 2020 (the date that is 30 days after the date of enactment of the legislation).
  2. The term “qualified disaster zone” is the portion of the qualified disaster area determined by the President to warrant individual or individual and public assistance from the federal government under the Robert T. Stafford Disaster Relief and Emergency Assistance Act by reason of the qualified disaster with respect to the qualified disaster area.
  3. The term “qualified disaster area” is an area with respect to which the President declared a major disaster from January 1, 2018, through February 18, 2020 (the date that is 60 days after the date of enactment of the legislation), under section 401 of the Stafford Act if the incident period of the disaster began on or before December 20, 2019 (the date of enactment). To avoid providing double benefits, the legislation excludes the California wildfire disaster area, for which similar relief was provided by the Bipartisan Budget Act of 2018.
  4. “The term ‘qualified disaster’ means, with respect to any qualified disaster area, the disaster by reason of which a major disaster was declared with respect to such area.”

G. Natural Resources Deductions & Credits

There were no significant developments regarding this topic during 2019.

H. Loss Transactions, Bad Debts, and NOLs

1. The Eleventh Circuit reversed a federal district court and held that the government failed to establish that an individual who reimbursed her ex-husband for federal taxes could not determine her tax liability under section 1341 for the year she paid the reimbursement.

In Mihelick v. United States, the taxpayer, Nora Mihelick, and her husband, Michael Bluso, divorced in 2005. During their marriage, they had both worked at Gotham Staple Company, a closely held Ohio corporation owned by her ex-husband’s family and for which her ex-husband served as chief executive officer. While their divorce was pending, her ex-husband’s sister, a minority shareholder in Gotham Staple Company, sued the taxpayer’s ex-husband and asserted claims of breach of fiduciary duty on the basis that he had excessively compensated himself at Gotham’s expense. Although the taxpayer initially resisted it, she and her ex-husband negotiated a provision in their separation agreement under which any liability arising from the litigation over her ex-husband’s alleged breach of fiduciary duty would be a marital liability for which they would be jointly and severally liable because, if such a liability came into existence, it would arise from the acquisition of marital assets during their marriage. In 2007, the taxpayer’s ex-husband settled the litigation pending against him and paid $600,000. The taxpayer resisted reimbursing her ex-husband, but after being advised by her attorney that she had an obligation to do so, she paid him $300,000 in 2009.

The taxpayer’s ex-husband determined his federal income tax liability for the year in which he made the $300,000 settlement payment by applying section 1341, which, if certain requirements are met, allows a taxpayer who must repay an amount previously included in income either to deduct the amount repaid or take a tax credit for the amount of tax overpaid in the year the income was included. On the taxpayer’s federal income tax return for 2009, the year in which she reimbursed her former husband, she determined her tax liability by applying section 1341 and claimed a refund, which the Service denied. Following the denial of her refund claim, the taxpayer brought a legal action seeking a refund in federal district court. The district court concluded that the taxpayer did not satisfy all requirements to determine her tax liability under section 1341, granted summary judgment for the government, and the taxpayer appealed.

In an opinion by Judge Rosenbaum, the Court of Appeals for the Eleventh Circuit held that the evidence supported the conclusion that the taxpayer satisfied all of the elements of section 1341 and that it was inappropriate for the district court to have granted summary judgment in favor of the government. The Eleventh Circuit remanded to the district court to determine whether there was any genuine issue of material fact concerning any of the elements of section 1341 and, if not, to enter judgment in favor of the taxpayer. If the district court concluded that there was a genuine issue of material fact, then the case had to proceed to trial. In either case, if the taxpayer prevailed, she would be entitled to determine her tax liability for 2009 by choosing whichever of the following provided her with the better result: (1) a deduction of the $300,000 she paid to her former husband in 2009 or (2) hypothetically recalculating her tax liability for the prior year in which she included the $300,000 in gross income by omitting the $300,000 from gross income, determining the amount by which her tax liability would have been reduced in that year, and taking the amount of the reduction as a credit in 2009.

To obtain the benefit of section 1341, four requirements must be satisfied. The court analyzed these requirements as follows:

The first requirement is that the taxpayer must have included an item in gross income for a prior year “because it appeared that the taxpayer had an unrestricted right to such item.” The government argued that this requirement was not met because the taxpayer’s former husband had no unrestricted right to the income in the year the couple included it in gross income because he had misappropriated the funds, and therefore she could not have had an unrestricted right to the income. The court rejected this argument because there was no proof her former husband had misappropriated the funds and the settlement agreement that resolved the litigation against him expressly disclaimed any wrongdoing. The court similarly rejected the argument that the taxpayer had no unrestricted right to her former husband’s income under the provisions of Ohio law concerning marital property: “What matters is whether [the taxpayer] sincerely believed she had a right to Bluso’s income, not the correctness of her belief.” The court concluded that there was enough evidence in the record to support the taxpayer’s sincere belief that she had an unrestricted right to his income in the years they were married.

The second requirement for a taxpayer to use section 1341 is that the taxpayer must have later learned that she actually “did not have an unrestricted right” to that income. According to the court, “[t]o make this showing, the taxpayer must demonstrate that she involuntarily gave away the relevant income because of some obligation, and the obligation had a substantive nexus to the original receipt of the income.” The court concluded that both aspects of this requirement were satisfied. In doing so, the court rejected the government’s argument that the fact that the taxpayer had reimbursed her former husband and had not paid her portion of the liability directly to the opposing party in the lawsuit precluded her from satisfying this requirement.

The third requirement of section 1341 is that the amount the taxpayer did not have an unrestricted right to and repays must have exceeded $3,000. The parties agreed that this requirement was satisfied.

The final requirement of section 1341 is that the amount the taxpayer did not have an unrestricted right to and repays must be deductible under another provision of the Internal Revenue Code. The court held that this requirement was met because her former husband was entitled to deduct the payment as a loss under section 165(c)(1) (losses incurred in a trade or business) and, by extension, the taxpayer was as well.

I. At-Risk and Passive Activity Losses

1. The taxpayer materially participated in an activity even though some of his hours were not hours when he was physically present at the business location.

In Barbara v. Commissioner, the taxpayers, a married couple, resided in Florida. The husband had owned and managed Barbara Trucking, a Chicago-area garbage-collection and waste-management business, which he sold for millions of dollars. He used the proceeds of the sale to start a lending business. The business had an office in Chicago with two full-time employees. Mr. Barbara divided his time between Florida and Chicago, spending 40% of his time in Chicago and 60% in Florida. He performed all executive functions for the lending business and worked 200 days per year. While in Chicago, he devoted 5.75 hours per day to the business and while in Florida devoted two hours per day. The Service proposed various adjustments for the returns filed by the taxpayers for 2009 through 2012.

One issue in the case was whether Mr. Barbara had materially participated in the lending business in 2009 through 2012. The Tax Court (Judge Morrison) held that he had materially participated. The court framed the question as whether Mr. Barbara had materially participated in the business under the seventh test in Regulation section 1.469-5T(a), which requires that the taxpayer participate more than 100 hours in the activity during the year and that the taxpayer’s participation be “regular, continuous, and substantial.” The court calculated that Mr. Barbara had devoted 460 hours per year while in Chicago (200 days x 40% x 5.75 hours) and 240 hours per year while in Florida (200 days x 60% x 2.0 hours), for a total of 700 hours, which more than met the 100-hour requirement. The court also concluded that his participation was regular, continuous, and substantial.

III. Investment Gain and Income

A. Gains and Losses

1. “Bitcoin is not a currency.” “No surprise” says Professor Omri Marian.

a. Notice 2014-21 “describes how existing general tax principles apply to transactions using virtual currency.” The Notice has two main components: (1) a substantive part (i.e., how Bitcoin transactions should be taxed) and (2) an information reporting part (i.e., how income on Bitcoin transactions should be reported and how tax can be collected).

(i) Substance. The substantive part of the Notice provides very few surprises. The most important conclusions are as follows.

(a) Bitcoin is not a currency for tax purposes; it is property. As such, gain and losses on the disposition of Bitcoins can never be “exchange gain or loss.” This may come as a disappointment to taxpayers who lost money in Bitcoin investments and may have hoped to have the losses classified as exchange-losses, and, as such, as ordinary losses. On the other hand, taxpayers who have disposed of appreciated investment positions in Bitcoins may enjoy capital gains treatment. Taxpayers who hold Bitcoin as inventory will be subject to ordinary gains and losses upon disposition.

(b) The receipt of Bitcoin in exchange for goods and services is taxable at the time of receipt. The amount realized is the U.S. dollar value of the Bitcoins received. The disposition of Bitcoin in exchange for goods and services is a realization and recognition event to the extent the value of Bitcoin has changed since the time it was acquired. Thus, if a taxpayer bought one Bitcoin for $500 and later used one Bitcoin to purchase a TV when Bitcoin was trading at $600, the taxpayer has a taxable gain of $100.

This part of the Notice has attracted some criticism from several commentators. A New York Times article summarized this critique, noting that characterizing Bitcoin as property

could discourage the use of Bitcoin as a payment method. If a user buys a product or service with Bitcoin, for example, the I.R.S. will expect the individual to calculate the change in value from the date the user acquired the Bitcoin to the date it was spent. That would give the person a basis to calculate the gains—or losses—on what the I.R.S. is now calling property.

This criticism is partially justified, although the result would have generally been the same had the Service decided to classify Bitcoin as a foreign currency. Under current law, U.S. taxpayers whose functional currency is the U.S. dollar (practically all U.S. taxpayers) must track their basis in any foreign currency they hold and recognize exchange gain or loss as soon as they dispose of the currency, but only to the extent their exchange gain or loss exceeds $200. Thus, the criticism might have some merit, as capital gains or losses are taxed from the first dollar while exchange gain or losses are subject to the $200 threshold. This could be corrected if a de minimis threshold would be made applicable to Bitcoin transactions as well, but it is not clear that there is any legal basis for the Service to do so. The only way to completely avoid taxation upon disposition of Bitcoin is to characterize it as a functional currency, which could only conceivably happen if the U.S. adopts Bitcoin as a legal tender. This is much to ask for, and certainly not within the power of the Service to decide.

(c) Since taxes are paid in U.S. dollars and not in Bitcoin, the Bitcoin value must be converted to U.S. dollars for purposes of determining gains and losses. Fair market value is determined by reference to the BTC/USD price quoted in an online exchange if “the exchange rate is established by market supply and demand.” The problem with this determination is that there are multiple such exchanges, and the BTC/USD spot price may vary significantly among such exchanges. For example, in March, 2013, the price difference between various exchanges varied by as much as $100, for an average trading price across exchanges of about $575. Taxpayers could cherry-pick their BTC/USD exchange rate and reduce tax gains or increase tax losses. Notice 2014-21 prescribes that BTC to USD conversion must be made “in a reasonable manner that is consistently applied.” It is not clear what “consistency” means in this context, and more guidance on this issue is needed.

(d) Mined Bitcoins are includable in gross income, and thus taxed, upon receipt. Bitcoins come into existence by a mining process. “Miners” use their computing resources to validate Bitcoin transactions and, in return, are compensated with newly created Bitcoin. Unsurprisingly, the Service concluded that such income is taxable upon receipt.

The Service did not explicitly rule on the character of mining income, but it is most likely ordinary under several possible theories: (1) It is income from services—miners are paid in newly generated Bitcoin for handling the bookkeeping of the Bitcoin public ledger. The Service describes an example of mining income as income received from using “computer resources to validate Bitcoin transactions and maintain the public Bitcoin transaction ledger.” This may imply that the Service views mining income as income from the provision of services. (2) It is wagering income—from a technical point of view mining is guessing the correct answer to a complex cryptography problem. (3) Mining pools—most miners mine through mining pools, where multiple individual miners pool together their computing resources in order to generate Bitcoins. Mining pools might be classified as partnerships for tax purposes. If the mining pool is a partnership, the mining pool itself is clearly in the business of mining Bitcoins. Any income from a trade or business of the partnership (the pool) passes through as ordinary income to the partners (the miners). If the mining pool is not a partnership, miners essentially rent out their computing capacity to the mining pool’s operator. Rental income is ordinary income.

(ii) Information reporting and backup withholding. Notice 2014-21, as expected, also concludes that payments in Bitcoins are subject to information reporting and backup withholding. Thus, a person who in the course of trade or business makes Bitcoin payments in excess of $600 to a non-exempt U.S. person must report such payments to the Service and to the recipient on the applicable Form 1099. The payments are also subject to backup withholding to the extent the payor is unable to solicit the requisite tax information from the payee.

This interpretation is perfectly reasonable, but its practical significance is left to be seen. The U.S. information reporting system is built on the assumption, among others, that parties to a taxable transaction know each other (or can reasonably obtain information about one another and send information to each other). As such, for example, taxpayers can send Forms 1099 to each other. The operation of Bitcoin defeats this assumption. Bitcoin is specifically designed to allow for exchange of value without having the parties to a transaction ever know each other. In fact, a Bitcoin payor is not always in a position to know whether payments he or she makes are made to the same person or to different people. Payors may have a hard time even deciding whether the $600 threshold is met. The default is backup withholding. It is not clear, however, how the Service can enforce reporting and withholding requirements when both parties to a transaction are anonymous both to the Service and to each other. The ramifications may be significant. Consider for example mining pools. In order to be in compliance, U.S. based mining pools would have to identify their participants by name (rather than by anonymous address), a result that the Bitcoin community is all but certain to dislike. The alternative—backup withholding by the pool operator in respect of the Bitcoin mined—would probably drive Bitcoin miners to mining pools operated by non-U.S. taxpayers. It will be interesting to see how these requirements pan out.

(iii) Unaddressed issues. The Service is well aware of the limited breadth of Notice 2014-21, and it has solicited comments from taxpayers. Some specific issues not addressed by the Notice that may be of significance are as follows:

  1. Whether Bitcoin and Bitcoin-wallets are financial assets and financial accounts, respectively, for purposes of FATCA and FBAR reporting requirements. This may not be of immediate relevance to most taxpayers due to the dollar amount thresholds applicable in such contexts, but as Bitcoin grows in popularity, such issues may become relevant.
  2. Whether Bitcoin service providers (such as wallet service providers, Bitcoin exchanges, Bitcoin mining pools and so on) are financial institutions for reporting, withholding, and FATCA purposes.
  3. Whether Bitcoin mining pools are entities for tax purposes. Some Bitcoin mining pools may conceivably be classified as entities separate from their owners for tax purposes and, as such, may qualify as partnerships. This may carry with it significant tax consequences to Bitcoin miners.
  4. Can Bitcoin be classified as a commodity for purposes of section 475(e), allowing dealers to elect mark-to-market accounting?

(iv) Summary. The Service guidance is clear, concise, and correct on the law. While some obscurities remain, most major interpretative issues are addressed. Notice 2014-21 does an excellent job explaining how transactions involving Bitcoin are taxed. It got all of the substantive issues right. In the context of information reporting, however, the Notice exposes the limitations of current tax law when it comes to collecting tax on Bitcoin transactions. While the Service got the information reporting part right as well, the practical ability of the Service to enforce such requirements may be limited in certain contexts. The main challenge remains in the area of collection. Time will tell whether the arsenal at the disposal of the Service is enough to deal with tax evasion through Bitcoin or whether Congress will have to supply the Service with additional ammo.

b. Are virtual currency accounts reportable on the FBAR? In a Service webinar broadcast on June 4, 2014, a Service program analyst in the Small Business/Self-Employed Division stated that the Service and the Treasury Department’s Financial Crimes Enforcement Network (FinCen) have been closely monitoring developments around virtual currencies such as Bitcoin. FinCen has said that virtual currency is not going to be reportable on the FBAR, at least for this filing season, but that could change in the future. More recently, according to the Journal of Accountancy, the AICPA Virtual Currency Task Force reached out to FinCEN regarding this issue, and “FinCEN responded that regulations (31 C.F.R. section 1010.350(c)) do not define virtual currency held in an offshore account as a type of reportable account. Therefore, virtual currency is not reportable on the FBAR, at least for now.”

c. The Service has announced a virtual currency compliance campaign. On July 2, 2018, the Service announced on its website—as one of five, large business and international compliance campaigns—a virtual currency campaign. The website describes the campaign as follows:

The Virtual Currency Compliance campaign will address noncompliance related to the use of virtual currency through multiple treatment streams including outreach and examinations. The compliance activities will follow the general tax principles applicable to all transactions in property, as outlined in Notice 2014-21. The IRS will continue to consider and solicit taxpayer and practitioner feedback in education efforts, future guidance, and development of Practice Units. Taxpayers with unreported virtual currency transactions are urged to correct their returns as soon as practical. The IRS is not contemplating a voluntary disclosure program specifically to address tax non-compliance involving virtual currency.

d. The Service has begun sending letters to taxpayers with virtual currency transactions who potentially failed to report their transactions properly. In July, 2019, the Service announced that it has begun sending letters to taxpayers with virtual currency transactions who potentially failed to report income or otherwise report the transactions properly. The Service expected that more than 10,000 taxpayers would receive the letters by the end of August, 2019. The Service urged those receiving the letters to take them very seriously and to take corrective action by amending returns and paying any tax and penalties due. The announcement stated that “[t]he names of these taxpayers were obtained through various ongoing IRS compliance efforts.”

e. If you are dealing with hard forks or airdrops of virtual currency you will want to read this Revenue Ruling. Revenue Ruling 2019-24 addresses whether a taxpayer has gross income as a result of either (1) a hard fork of a cryptocurrency that the taxpayer owns if the taxpayer does not receive units of a new cryptocurrency or (2) an airdrop of a new cryptocurrency following a hard fork if the taxpayer receives units of the new cryptocurrency. The Ruling provides definitions of a hard fork and an airdrop, which are very technical and require a detailed understanding of the mechanisms through which virtual currency transactions are carried out. The Ruling concludes that a taxpayer does not have gross income in the first situation but does have gross income in the second.

f. The draft Schedule 1 for the 2019 Form 1040 asks about virtual currency transactions. On October 10, 2019, the Service released a draft of Schedule 1 (Additional Income and Adjustments to Income) for the 2019 individual income tax return on Form 1040. The revised Schedule 1 asks the following question at the top of the form: “At any time during 2019, did you receive, sell, send, exchange, or otherwise acquire any financial interest in any virtual currency?”

2. ♫♪ We’re off to see the wizard, the wonderful wizard of QOZ! ♪♫

Section 13823 of the TCJA added sections 1400Z-1 and 1400Z-2 to the Code relating to qualified opportunity zones (QOZs) and qualified opportunity funds (QOFs). New sections 1400Z-1 and 1400Z-2 are designed to encourage investors to free up capital and invest in economically distressed census tracts (i.e., QOZs) by providing federal income tax benefits to taxpayers who realize capital gains and reinvest them in certain funds (i.e., QOFs) that, in turn, invest in businesses and real estate located in these designated communities. More than 8,700 census tracts have been designated as QOZs. There are designated QOZs in all 50 states, the District of Columbia, and several U.S. territories. Sections 1400Z-1 and 1400Z-2 are effective December 22, 2017. To satisfy this effective date, it appears that the qualified reinvestment in a QOF must take place after December 22, 2017.

In October, 2018, the Treasury Department and the Service published its first set of Proposed Regulations under section 1400Z-2 and published a second set of Proposed Regulations in May, 2019. These two sets of Proposed Regulations are generally proposed to be effective on the date they are published as final regulations, but taxpayers can rely on them before that date if applied in their entirety and in a consistent manner.

a. Taxpayers Eligible to Use Section 1400Z-2. The tax benefits of investing in a QOF are set forth in section 1400Z-2. Virtually any type of taxpayer having a qualifying capital gain (“eligible gain”) may qualify for the tax benefits provided by section 1400Z-2 including individuals, C corporations (including regulated investment companies and real estate investment trusts), partnerships, S corporations, and trusts and estates. The Preamble to the Proposed Regulations states that eligible taxpayers also include common trust funds described in section 584 as well as qualified settlement funds, disputed-ownership funds, and other entities taxable under the section 468B Regulations.

b. Overview of Tax Incentives for Investing in QOFs. The tax incentives provided by section 1400Z-2 are summarized briefly below.

(i) Deferral of Capital Gain to Extent Invested in QOF Within 180 Days. Generally, section 1400Z-2 allows taxpayers to defer capital gains (long-term or short-term) to the extent the gains are invested in a QOF within 180 days of realizing the capital gain.

(ii) Investment in QOF Held for at Least Five YearsTen-Percent Exclusion. If the investment in the QOF is held for at least five years, then the taxpayer can exclude from gross income ten percent of the original deferred capital gain.

(iii) Investment in QOF Held for at Least Seven YearsAdditional Five-Percent Exclusion. If the investment in the QOF is held for at least seven years, then the taxpayer can exclude from gross income an additional five percent of the deferred capital gain for a total exclusion of 15% of the original deferred capital gain. Because gain deferred under section 1400Z-2 is taxed upon the earlier of the date the investment in the QOF is sold (or disposed of in a taxable transaction) or December 31, 2026, a taxpayer must invest in a QOF by December 31, 2019, to meet the seven-year holding period and thereby receive the additional five-percent exclusion.

(iv) Remaining Deferred Capital Gain Taxed No Later Than December 31, 2026. Any remaining deferred capital gain is generally taxed on the earlier of (1) the date the investment in the QOF is sold (or disposed of in a taxable transaction) or (2) December 31, 2026.

(v) Investment In QOF Held for at Least Ten YearsPost-Acquisition Gain Excluded from Income. For qualified investments in a QOF held for at least ten years, the taxpayer may elect to exclude from gross income any gain from post-acquisition appreciation (i.e., may elect to increase the basis of the fund to the fair market value of the fund on the date the investment in the fund is sold or exchanged).

c. Acquisition of a Qualifying QOF Interest. The discussion of investment in QOFs discussed in this outline assumes that the taxpayer invested cash in the QOF because it is generally presumed that the vast majority of investments in QOFs will be in cash. However, the Proposed Regulations provide detailed guidelines for how these rules would operate if the taxpayer transferred noncash property in return for a qualifying QOF interest. A taxpayer may not acquire a qualifying QOF interest in return for providing services to the QOF. A taxpayer can acquire a qualifying QOF interest from someone other than the QOF.

d. Qualifying Capital Gains Eligible for Deferral and or Exclusion. The requirements for capital gains to be eligible for deferral or exclusion are summarized below.

(i) “Capital” Gains Eligible for Deferral Treatment Under Section 1400Z-2. Proposed Regulation section 1.1400Z-2(a)-1(b)(2) provides that a gain eligible for deferral or exclusion treatment under section 1400Z-2 (“eligible gain”) is generally a gain that (1) is “treated as capital” for federal income tax purposes, (2) would otherwise have been recognized for federal income tax purposes before January 1, 2027, except for the deferral under section 1400Z-2, and (3) does not arise from a sale or exchange with a “related party.” The Preamble to the Proposed Regulations provides that even the “capital gain” portion (if any) of a dividend would generally qualify for deferral treatment under section 1400Z-2.

Although all gains treated as “capital gains” under the Code will generally be “eligible gains,” there are certain limitations on capital gains from section 1256 contracts and other gains that are part of an “offsetting-position” transaction.

(ii) Short-Term Capital Gains. There is no prohibition for qualifying short-term capital gains. However, if a short-term capital gain is deferred by a qualifying investment in a QOF, it will retain its short-term capital gain treatment when the deferred gain is ultimately recognized.

(iii) Gains Arising from a Sale to a “Related Party” Do Not Qualify. For this purpose, persons are related to each other if they are described in section 267(b) or section 707(b), determined by substituting 20% for 50% wherever it appears in those sections.

(iv) Capital Gains to Owners Resulting from Operating or Liquidating Distributions from Their C Corporations, S Corporations, or Partnerships. Generally, a capital gain is triggered under section 301 or section 731 if a C corporation, S corporation, or partnership makes an actual or deemed cash distribution in excess of the owner’s basis in the stock or partnership interest. A capital gain from such a distribution should generally be an “eligible gain” for purposes of deferral under section 1400Z-2. However, if the distributee-owner and the distributing entity meet the 20% ownership test for “related parties” discussed above (a fairly common situation), the gain on the distribution would not qualify for deferral.

(v) Capital Gains Under Section 1231. Proposed Regulation section 1.1400Z2(a)-1(b)(2)(iii) states:

The only gain arising from section 1231 property that is eligible for deferral under section 1400Z-2(a)(1) is capital gain net income for a taxable year. This net amount is determined by taking into account the capital gains and losses for a taxable year on all of the taxpayer’s section 1231 property. The 180-day [Reinvestment P]eriod . . . with respect to any capital gain net income from section 1231 property for a taxable year begins on the last day of the taxable year.

(a) Property Subject to Section 1231. Generally, section 1231 gains and losses arise from the sale or exchange or compulsory or involuntary conversion of “property used in the trade or business.” Section 1231(b)(1) generally defines “property used in a trade or business” as property used in a trade or business that is held for more than one year that is either (1) subject to the allowance for depreciation under section 167 or (2) real property. However, this category also includes timber held for more than one year when the taxpayer elects to treat the cutting as a sale and timber sold with a retained economic interest under section 631; coal or domestic iron ore sold with a retained economic interest as described under section 631; certain livestock; and certain unharvested crops.

(b) Section 1231 Tax Treatment. If, for the tax year, a taxpayer’s total section 1231 gains from sales or exchanges (i.e., those in the so-called “main hotchpot”) exceed the taxpayer’s total section 1231 losses, the gains are treated as long-term capital gains and the losses are treated as long-term capital losses. By contrast, if for the tax year a taxpayer’s total section 1231 losses exceed the taxpayer’s section 1231 gains, the gains are treated as ordinary income and the losses are treated as ordinary losses. As noted above, the Proposed Regulations provide that only a taxpayer’s “capital gain net income” under section 1231 is eligible for deferral under section 1400Z-2(a)(1). The term “capital gain net income” seems to suggest that only the “net” section 1231 gain amount is eligible for deferral. Assuming this interpretation is correct, if for the tax year a taxpayer had a single section 1231 gain of $100 and a single section 1231 loss of ($80), only the net section 1231 gain of $20 ($100 less $80) would be eligible for deferral. However, since the entire section 1231 gain of $100 is a long-term capital gain under a literal reading of section 1231(a)(1), some have argued that the entire $100 should be available for deferral.

Several professional groups have submitted comment letters to the Treasury Department recommending that the final regulations clarify that once a taxpayer has a net section 1231 gain, then each “gross” section 1231 gain ($100 in the above example) would be available for deferral if that amount is invested in a QOF.

(c) 180-Day Reinvestment Period for Net section 1231 Gains. For any given tax year, whether a taxpayer has a net section 1231 gain (qualifying for deferral) cannot be determined until the end of the tax year. Consequently, as noted above, the Proposed Regulations provide that the 180-day reinvestment period to invest in a QOF with respect to a net section 1231 gain does not begin until the last day of the taxable year.

Practice Alert! If, for example, a calendar-year taxpayer has only a single gain from the sale of a section 1231 asset during 2019, the earliest the taxpayer could purchase a qualifying interest in a QOF in order to defer the net section 1231 gain would be December 31, 2019. Presumably, unless we get further guidance on this issue, the taxpayer in this example would have to wait until December 31, 2019, to reinvest in the QOF even if the taxpayer knew in advance that there would be no section 1231 losses during the remainder of the year.

Several professional organizations (e.g., AICPA, ABA, and the State Bar of Texas Tax Section) have submitted comments to the Treasury Department recommending that the final regulations provide a more flexible 180-day period for section 1231 gains. For example, several of the comments recommended an option to start the 180-day period on the date of the sale of the section 1231 property (particularly if the taxpayer was able to predict with some certainty that it would end up with a net section 1231 gain by the end of the year).

(d) Section 1231 Gains Generated by Partnerships and S Corporations. Net section 1231 gains and losses generated by a pass-through entity (e.g., a partnership or S corporation) pass through to the owners as “separately stated” items. The owners (partners and S corporation shareholders) then combine the net section 1231 gains and losses that pass through with their own section 1231 gains and losses to determine whether they have an overall net section 1231 gain or a net section 1231 loss on their individual returns. Consequently, even if the pass-through entity has a net section 1231 gain at the entity level, it is entirely possible that the net section 1231 gain passing through to the owner, when combined with the owner’s separate section 1231 losses, could ultimately be taxed to the owner as a “net” section 1231 loss.

This treatment of net section 1231 gain passed through by a partnership or S corporation raises a question as to whether a partnership or an S corporation can make the election at the entity level to defer the net section 1231 gain (determined at the entity level) by investing in a QOF. According to media reports on the ABA Tax Section’s May meeting, Bryan Rimmke, an attorney-adviser in the Treasury Department’s Office of Tax Legislative Counsel, stated that “the government allows a partnership to net its gains against its losses for section 1231 purposes, and if it ends up with a net gain, the partnership can elect to invest that gain into a qualified opportunity fund.” It was reported that Mr. Rimmke agreed that this netting of section 1231 gains and losses at the partnership level is allowed for purposes of reinvesting the net gain in a QOF “[e]ven if a partnership doesn’t have a per se [section] 1231 netting.” Hopefully the Service will provide clear guidance on this issue in the final regulations.

(e) Impact of Recapture Rules on Eligible Section 1231 Gain. If, and to the extent, a net section 1231 gain is recharacterized as ordinary income under the depreciation recapture provisions of section 1245 or section 1250 or under the five-year look-back rule under section 1231(c), the ordinary income portion would not be eligible for deferral under section 1400Z-2.

Section 1231(c) generally provides that a taxpayer’s net section 1231 gain for the current year will be recharacterized as ordinary gain to the extent of the taxpayer’s net section 1231 losses recognized in the preceding five years. However, section 1231(c) is a section 1231 loss “look-back” rule, not a section 1231 loss “look-forward” rule. To illustrate, assume that for 2019 a taxpayer (1) has had no net section 1231 losses in the preceding five years, (2) in 2019 has already recognized a single section 1231 gain of $100, and (3) is now considering selling a single section 1231 asset for a loss of ($90). If the taxpayer sells the section 1231 loss asset before the end of 2019 generating a section 1231 loss of ($90), the taxpayer would have a “net” section 1231 gain for 2019 of $10 ($100 less $90) which would qualify for deferral under section 1400Z-2. However, if the taxpayer waits until 2020 to recognize the section 1231 loss of ($90), she will have a net section 1231 gain for 2019 of $100 eligible for deferral under section 1400Z-2. Moreover, if taxpayer has no other section 1231 transactions in 2020 other than the section 1231 loss of ($90), she would then be able to deduct fully the ordinary loss of ($90) against all other 2020 income. In this situation, the five-year look-back rule under section 1231(c) would not apply to 2020 because that rule applies only when there are net section 1231 losses reported in the preceding five years.

e. General Tax Benefits of Investing in Qualified Opportunity Funds (QOFs). The tax benefits provided by section 1400Z-2 for those investing in QOFs are described in more detail below.

(i) Gain-Deferral Benefits Under section 1400Z-2. A taxpayer may defer recognition of a qualifying capital gain by investing the amount of the gain in a QOF within 180 days of realizing the capital gain. For example, assume that a taxpayer sold a capital asset for $100 with a basis of $10 (realizing a $90 qualifying capital gain). The taxpayer could defer 100% of the $90 capital gain by investing $90 (i.e., the amount of the gain) in a QOF within 180 days. The initial basis of the QOF investment acquired as a result of the reinvestment of the taxpayer’s qualified capital gain is zero. So, in the above example, the taxpayer’s initial basis in the QOF investment is zero, even though the taxpayer paid $90 for it.

(a) Maximum Period of Gain Deferral. The deferred gain (e.g., $90 in the above example) must be recognized on the earlier of (1) December 31, 2026 (whether or not the taxpayer sells the QOF interest) or (2) the date the taxpayer sells or exchanges the interest in the QOF.

(b) Maximum Gain Recognized When Deferred Gain Triggered. When the deferred gain is triggered, the maximum amount of deferred gain that will be recognized is the lesser of (1) the amount of gain originally deferred or (2) the fair market value of the QOF investment as determined on the recognition date, over the taxpayer’s basis in the QOF investment. Again using the above example, assume that after four years the taxpayer sold the QOF investment for $75. This would result in a deferred gain of only $75 being triggered even though the original deferred gain was $90. This generally means that, if on the recognition date the value of the QOF interest has dropped below the initial investment amount in the QOF interest (e.g., in the above example that would be below $90), the amount of the deferred gain recognized will generally be reduced by the post-acquisition loss in value.

(ii) Reduction of Deferred Gain Based on Five- or Seven-Year Holding Periods. As mentioned previously, after the taxpayer holds the QOF investment for at least five years, ten percent of the deferred gain will be excluded from the taxpayer’s gross income. If the QOF investment is held at least seven years, then an additional five percent (a total of 15%) of the deferred gain will be excluded from the taxpayer’s gross income. This exclusion results from the taxpayer getting an automatic increase in the basis of the QOF interest of ten percent of the deferred gain at five years and an additional increase of five percent at seven years. Again using the above example, after the taxpayer has held the QOF investment for five years, her basis goes from zero to $9 (i.e., ten percent of the deferred gain of $90), and after holding it for seven years, her basis goes to $13.50 (i.e., 15% of the deferred gain of $90). As noted earlier, because gain deferred under section 1400Z-2 is taxed upon the earlier of the date the investment in the QOF is sold (or disposed of in a taxable transaction) or December 31, 2026, a taxpayer must invest in a QOF by December 31, 2019, to meet the seven-year holding period and thereby receive the additional five-percent exclusion.

Impact of Potential Increases in Capital Gains Tax Rates. Even in the best case scenario, 85% of the original deferred capital gain will be taxed no later than December 31, 2026, at whatever capital gains rates exist in 2026. If the current effective maximum long-term capital gains rate of 23.8% is increased between now and 2026, the increase in the capital gains rates would dilute the tax benefit of the tax deferral. Assuming a 15% deferred gain exclusion, it would appear that the top effective capital gains rate would have to be increased to above 28% (i.e., 28% x 85% equals 23.8%) before the top effective rate would be greater than the current top effective capital gains rate of 23.8%.

(iii) 100% Gain Exclusion After Holding QOF for Ten Years. After the taxpayer holds the QOF investment for at least ten years, the taxpayer can exclude 100% of the gain realized from the sale or exchange of the QOF interest. This gain, in essence, represents the appreciation that occurred in the QOF investment after the taxpayer purchased it. To receive the benefit of this exclusion, the taxpayer must sell the interest in the QOF before 2048. To illustrate, recall in the above example that the taxpayer sold a capital asset for $100 with a basis of $10 (realizing a $90 qualifying capital gain) and deferred the gain by investing $90 in a QOF within 180 days. If the taxpayer holds the QOF investment for at least ten years, sells it for $150, and elects to step the basis up to the fair market value of the QOF investment on the date of the sale as provided in section 1400Z-2(c), the taxpayer could exclude 100% of the $60 gain (i.e., sales proceeds of $150 less the initial investment of $90 in the QOF).

(a) Generally No Taxable Gain Triggered on Investment in QOF After Ten-Year Holding Period. The sale, exchange, or other disposition of a QOF investment (acquired solely to defer previous gain) that is held by the taxpayer for at least ten years should not trigger any taxable gain because (1) all of the initial deferred gain reflected in the investment in a QOF must be fully recognized no later than December 31, 2026, and (2) 100% of the post-acquisition gain is excluded if the QOF investment is held at least ten years.

(b) Ten-Year Rule Applies Only to QOF Investment That Allowed Taxpayer to Defer Initial Capital Gain. The only portion of the investment in the QOF that qualifies for this 100% gain exclusion is the portion of the investment that allows the taxpayer to defer a previous capital gain. If a taxpayer invests in a QOF and only a portion of the investment is used to defer a previous capital gain, then the investment in the QOF will be treated as two separate investments. For example, again recall the facts in the previous hypothetical in which the taxpayer sold a capital asset for $100 with a basis of $10 (realizing a $90 qualifying capital gain). Assume further that the taxpayer used the entire sales proceeds of $100 to purchase an interest in a QOF for $100. In that event (1) the QOF interest representing $90 of the purchase price (i.e., the amount of gain deferred) will be treated as a separate QOF investment and can qualify for the 100% exclusion if held at least ten years, and (2) the QOF interest representing $10 of the purchase price will likewise be treated as a separate QOF investment but will not qualify for the 100% exclusion. In this example, although the separate QOF investment represented by the $90 will qualify for the 10 to 15% bump-up in basis if held five or seven years, the separate QOF investment represented by the $10 will not qualify for any basis bump. Thus, an investor who simply invests in a QOF (without attempting to use the investment to defer previously-realized capital gain) will receive no special tax treatment under section 1400Z-2 when the investor later sells the QOF interest.

(c) QOF’s Sale of “Qualifying Ozone Business Property” After Ten Years. Generally, section 1400Z-2 allows a taxpayer who has met the ten-year holding period requirement to exclude 100% of the gain resulting from the sale of the taxpayer’s QOF interest. Thus, for example, if a taxpayer meeting the ten-year holding period requirement sold S corporation stock or a partnership interest in an entity that was a QOF and elected to step up the basis to fair market value, the entire gain would be excluded. Moreover, it appears that the entire gain on the sale a QOF partnership interest would be excluded even if the partnership held so-called “hot assets” under section 751(a).

Sale of Assets by QOF. The Proposed Regulations provide special rules for allowing an investor to exclude pass-through “capital gains” and pass-through “capital gain net income from section 1231 property” triggered by a QOF selling its qualifying ozone business property after the ten-year holding period. Note: Even if the ten-year holding period is satisfied, it appears that the QOF investor could not exclude pass-through ordinary gain (e.g., sections 1245 and 1250 depreciation recapture gain, cash-basis receivables, inventory gain, etc.) from the sale of the assets by the QOF. Consequently, if the investor sells an ownership interest in a QOF (S corporation stock or partnership interest) after meeting the ten-year holding period requirement, the taxpayer can exclude 100% of the gain. By contrast, if the QOF sells the assets of the business, any ordinary income passing through to the QOF investor will be fully taxed.

(iv) Gain Triggered On Disposition of Entire Interest in QOF May Be Deferred if Reinvested in QOF Within 180 Days, But Reinvestment Starts New Holding Period. The Preamble to the Proposed Regulations states:

If a taxpayer acquires an original interest in a QOF in connection with a gain-deferral election under section 1400Z-2(a)(1)(A), if a later sale or exchange of that interest triggers an inclusion of the deferred gain, and if the taxpayer makes a qualifying new investment in a QOF, then the proposed regulations provide that the taxpayer is eligible to make a section 1400Z-2(a)(2) election to defer the inclusion of the previously deferred gain. Deferring an inclusion otherwise mandated by section 1400Z-2(a)(1)(B) in this situation is permitted only if the taxpayer has disposed of the entire initial investment. . . .

The Preamble also provides:

[I]f an investor disposes of its entire qualifying investment in QOF 1 and reinvests in QOF 2 within 180 days, the investor’s holding period for its qualifying investment in QOF 2 begins on the date of its qualifying investment in QOF 2, not on the date of its qualifying investment in QOF 1.

f. “Inclusion Events” That Trigger Deferred Gain. The events that trigger recognition of a taxpayer’s deferred gain are described below.

(i) Deferred Gain “Inclusion Events.” Section 1400Z-2(b)(1)(A) generally requires the deferred gain to be recognized if the investment in the QOF is “sold or exchanged” before December 31, 2026. (Note: The following “inclusion events” are relevant only for the deferred gain through December 31, 2026, because any deferred gain remaining after application of the five- and seven-year exclusion rules must be recognized no later than December 31, 2026, even if the taxpayer is still holding the QOF investment.) Proposed Regulation section 1.1400Z2(b)-1(c) includes a long list of transactions (called “inclusion events”) that trigger all or a portion of the deferred gain reflected in an investment in a QOF. The list of “inclusion events” is long, technical, detailed, and the following is merely an overview of selected provisions. Generally, the “inclusion events” under the Proposed Regulations fall into two categories: (1) certain transactions that reduce the taxpayer’s equity interest in the QOF and (2) certain distributions of property from the QOF.

(a) Overview of “Equity Reductions” in Taxpayer’s Interest in QOF That Could Trigger Deferred Gain. Transactions that reduce a taxpayer’s equity interest (directly or indirectly) in the QOF that could trigger all or a portion of the deferred gain include (1) dispositions of all or a portion of an interest in a QOF by sale or exchange, (2) disposition by gift (even if the donee is a tax-exempt organization), (3) liquidation of the QOF, (4) certain liquidations of an owner of an interest in a QOF, (5) disposition of an interest in a partnership that is an owner in a QOF, and (6) an aggregate change in ownership in excess of 25% of an S corporation that holds an interest in a QOF.

The Proposed Regulations also provide that the deferred gain will be triggered if a taxpayer claims a worthlessness deduction under section 165(g) with respect to a qualifying QOF investment.

(b) Overview of Certain Distributions of Property That Could Trigger Deferred Gain. An inclusion event could occur whenever there is an actual or deemed distribution of property (including cash) by a QOF partnership or corporation in which the distributed property has a FMV in excess of the taxpayer’s basis in the QOF partnership or corporation. This could include a distribution from a QOF corporation or partnership that exceeds the owner’s basis and is thus taxed as a sale or exchange under sections 301, 731, or 1368.

(c) More Details on Inclusion Events. Please see Proposed Regulation section 1.1400Z2(b)-1(c) for additional details, including a complete list of inclusion events.

(ii) Overview of Certain Transactions That Do Not Trigger Deferred Gain. The Proposed Regulations also identify transactions that generally are not inclusion events, including (1) certain transfers of an investment in a QOF upon the death of a taxpayer (however, the deferred gain is treated as income in respect of a decedent under section 691 when triggered, but the recipient receives the decedent’s holding period in the QOF for purposes of the five-, seven-, and ten-year rules), (2) the contribution of an ownership interest in a QOF to a grantor trust, (3) section 721 contributions (i.e., contributions of property to a partnership in exchange for a partnership interest), and (4) the election, revocation, or termination of S corporation status.

If certain rigid requirements are satisfied, a QOF may be able to sell all or a portion of its qualifying opportunity zone property without triggering a penalty on the QOF for failing to invest 90% of its assets in qualified opportunity zone property if the proceeds are reinvested in qualifying opportunity zone property during a 12-month testing period. However, it appears under the Proposed Regulations that any gain (including capital gains) recognized by the QOF on the sale and reinvestment of its qualified opportunity zone property will pass through and be taxed to an investor in the QOF who has not held his or her interest for at least ten years. As previously discussed, if the investor has held the QOF interest for at least ten years, the pass-through capital gains or net section 1231 gains generated by the QOF should be tax-free to the investor.

g. Timing and Reporting Requirements for Deferred Gains Invested in a QOF. The timing and reporting requirements for deferred gains invested in a QOF are summarized below.

(i) The 180-Day Reinvestment Requirement. Generally, for an eligible capital gain to be deferred under section 1400Z-2, the taxpayer must purchase a qualifying investment in a QOF no later than 180 days following the date of the sale, exchange, or other disposition that generated the eligible gain. However, the Proposed Regulations provide that generally the first day of the 180-day period is the date on which the gain would be recognized for federal income tax purposes, without regard to the deferral available under section 1400Z-2. There are at least two examples in which the starting date of the 180-day period begins after the date of the sale or exchange: (1) net section 1231 gains—as discussed above—and (2) pass-through entities—if a partnership or S corporation has an “eligible gain,” the pass-through entity may elect to defer the gain and invest in a QOF within 180 days of the disposition. However, if the pass-through entity does not elect to defer the gain, each owner has the option to elect to defer the owner’s respective portion of the pass-through eligible gain by directly investing in a QOF. In this latter situation, the beginning of the 180-day period for the owners generally begins on the last day of the pass-through entity’s tax year.

(ii) Election MechanicsForm 8949. A taxpayer must affirmatively elect to defer an eligible gain by making the election on Form 8949 (“Sales and Other Dispositions of Capital Assets”) in accordance with the Form’s instructions by reporting the eligible gain and entering “Z” in column (f). In addition, the instructions to the 2018 Form 8949 provide:

If the gain is reported on Form 8949, do not make any adjustments for the deferral in column (g). Report the deferral of the eligible gain on its own row of Form 8949 in Part I with box C checked or Part II with box F checked (depending on whether the gain being deferred is short-term or long-term). If you made multiple investments in different QO Funds or in the same QO Fund on different dates, use a separate row for each investment.

(iii) Service Says Election to Defer Gain Can Be Made on an Amended Return. On its website, the Service answered this question in a segment entitled “Opportunity Zones FAQs” which contains the following Q&A: “Q. Can I still elect to defer tax on that gain if I have already filed my tax return? A. Yes, but you will need to file an amended return, using Form 1040-X and attaching Form 8949.”

3. Tax Court holds that individuals’ amount realized from foreclosure sale of real property was bid price at foreclosure sale and, taking into account their basis in foreclosed properties, they realized a $4.3 million long-term capital loss.

In Breland v. Commissioner, Charles and Yvonne Breland, a married couple, sold real property in both 2003 and 2004, deposited the proceeds with an intermediary, and acquired other real property. They treated the transactions in 2003 and 2004 as like-kind exchanges eligible for deferred recognition of gain under section 1031. One of the properties that the taxpayers acquired in the like-kind exchange in 2004 was a lot on Dauphin Island, Alabama (Dauphin Island 1), for which they reported an adjusted basis of $6,689,113. In 2005, they acquired a second property on Dauphin Island (Dauphin Island 2) for $5,613,287. They financed the purchase of Dauphin Island 2 with a recourse mortgage loan from Whitney Bank in the amount of $11.2 million. The taxpayers used this loan, which was secured by both Dauphin Island 1 and Dauphin Island 2, not only to acquire Dauphin Island 2, but also to refinance indebtedness they had incurred with respect to Dauphin Island 1. In early 2009, the taxpayers defaulted on the loan from Whitney Bank, which had an outstanding balance at that time of $10.7 million. Whitney Bank foreclosed on the loan and held a foreclosure sale in 2009 at which Whitney Bank was the high bidder with a bid of $7.2 million. The taxpayers later filed for chapter 11 bankruptcy protection in federal court, and Whitney Bank filed a proof of claim in that proceeding for $6.3 million.

On their federal income tax return for 2009, the taxpayers initially reported a capital loss from the sale of Dauphin Island 1 and Dauphin Island 2 of $1.8 million, which they determined by treating the outstanding loan balance (approximately $10.7 million) as their amount realized and comparing it to their adjusted bases in the properties. They subsequently filed an amended return for 2009 on Form 1040X on which they reported a capital loss from the sale of Dauphin Island 1 and Dauphin Island 2 of $5.3 million, which they determined by treating the bid price at the foreclosure sale (approximately $7.2 million) as their amount realized and comparing it to their adjusted bases in the properties. The Service challenged their determination of both their amount realized and their adjusted bases in the properties sold at the foreclosure sale. According to the Service, the taxpayers had overstated the amount of their capital loss from the foreclosure sale.

a. The amount realized in the foreclosure sale was the $7.2 million bid price, not the full $10.7 million outstanding loan balance. The Tax Court (Judge Pugh) first concluded that the amount realized by the taxpayers from the 2009 foreclosure sale of Dauphin Island 1 and Dauphin Island 2 was the $7.2 million bid price for which the properties were sold, not the $10.7 million outstanding loan balance. Generally, under section 1001(b), a taxpayer’s amount realized from the sale or exchange of property is the amount of money received plus the fair market value of any property received. According to Regulation section 1.1001-2(a)(1), a taxpayer’s amount realized also includes the amount of any liabilities from which the taxpayer is discharged as a result of transferring the property. The Tax Court explained that this rule applies in the case of nonrecourse debt, that is, the amount realized includes the full amount of the nonrecourse debt that is discharged by transferring the property. In the case of recourse debt such as the debt in this case, however, the taxpayer’s amount realized is limited to the fair market value of the property. The court relied for this proposition on Regulation section 1.1001-2(a)(2), which provides that “[t]he amount realized on a sale or other disposition of property that secures a recourse liability does not include amounts that are (or would be if realized and recognized) income from the discharge of indebtedness under section 61(a)(12).”

The Service argued that the $7.2 million bid price for the Dauphin Island properties at the foreclosure sale did not establish their fair market value because the sale was compelled and not a sale between a willing buyer and a willing seller. According to the court, however, “in the case of mortgaged property sold at a foreclosure sale, we presume fair market value to be the bid price, absent clear and convincing evidence to the contrary.” In this case, the court concluded there was no clear and convincing evidence to the contrary, the bid price established the fair market value of the foreclosed properties, and the amount realized by the taxpayers was $7.2 million. In reaching this conclusion, the court rejected the Service’s argument that, if the bid price is treated as the amount realized, then the taxpayers should have recognized discharge of indebtedness income of approximately $5.5 million, which was the remaining loan balance. According to the court, the preponderance of the evidence, including Whitney Bank’s filing of a proof of claim in the taxpayers’ bankruptcy proceeding, suggested that the remaining loan balance had not been discharged.

b. The aggregate basis the taxpayers had in the properties sold at the foreclosure sale was $11.5 million, and therefore they realized a capital loss of $4.3 million. The Tax Court concluded that the taxpayers had not adequately substantiated their basis in the Dauphin Island 1 property. Specifically, the court concluded that they had not adequately substantiated their basis in the relinquished property they had exchanged for Dauphin Island 1 and therefore had not adequately substantiated the basis that carried over to Dauphin Island 1. Accordingly, the court reasoned that their basis in Dauphin Island 1 was $5.9 million, which was the amount of money they had paid for it plus the amount of indebtedness they had incurred to purchase it, less the amount of liabilities satisfied in the transaction in which they acquired Dauphin Island 1. Their basis in Dauphin Island 2 was $5.6 million, the amount they had paid for the property. Therefore, their aggregate basis in the two properties was $11.5 million. Their capital loss from the foreclosure sale was the amount by which their $11.5 million adjusted basis in the properties exceeded their $7.2 million amount realized, or $4.3 million. Because they had held both properties for more than one year, the loss was a long-term capital loss.

c. Anti-deficiency statutes must be considered. As the Tax Court pointed out in Breland, if the debt secured by foreclosed properties is nonrecourse debt, then the taxpayers’ amount realized from the foreclosure sale generally will be the full amount of the nonrecourse debt. In determining whether debt is nonrecourse, it is necessary to consider so-called state anti-deficiency statutes, which prohibit lenders from holding borrowers responsible for the difference between the amount of the mortgage loan secured by the property and the price for which the property is sold at the foreclosure sale. If a state anti-deficiency law applies, then the debt will be treated as nonrecourse debt and the taxpayers’ amount realized from the foreclosure sale generally will be the full amount of the debt. For example, in Simonsen v. Commissioner, the Tax Court held that debt secured by real property sold by the taxpayers in a short sale was nonrecourse debt when California’s anti-deficiency statute precluded the lender from pursuing the taxpayers for the balance of the loan that was not satisfied by the short sale. For this reason, the court in Simonsen treated the full amount of the mortgage loan as the taxpayers’ amount realized in the short sale.

B. Interest, Dividends, and Other Current Income

There were no significant developments regarding this topic during 2019.

C. Profit-Seeking Individual Deductions

1. The Service gets hoisted by its own petard, and in the process, we get an unusual lesson in “following the money” for purposes of the interest expense deduction limits under section 163.

Although the facts are a bit convoluted in Lipnick v. Commissioner, the Tax Court (Judge Lauber) reaffirmed the “follow the money” principles for determining deductible interest expense under section 163, including for debt-financed partnership distributions and the aftermath thereof. The taxpayer’s father held membership interests in several limited liability companies (LLCs) classified as partnerships for federal income tax purposes. The LLCs owned and managed very profitable residential rental properties in the Washington, D.C., area. The LLCs made nonrecourse debt-financed distributions to the taxpayer’s father totaling approximately $80 million. The taxpayer’s father used the proceeds of these debt-financed distributions to purchase investment assets that he held personally. Similarly, in 2012, the taxpayer’s father received, directly and indirectly, yet another debt-financed distribution of approximately $1.7 million from a residential rental property limited partnership (LP) in which he and his family limited partnership (FLP) were partners. The taxpayer’s father also used the proceeds of this debt-financed distribution to purchase investment assets that he held personally.

For the years 2009–2012, pursuant to Notice 89-35 and Temporary Regulation section 1.163-8T(a)(4)(i)(C), the taxpayer’s father reported his allocable share of the LLCs’ and the LP’s interest expense (including the LP’s interest expense passed through his FLP) as investment interest for purposes of the section 163(d)(1) limitation on the deductibility of investment interest. (Incidentally, it appears that the taxpayer’s father was able to deduct his entire allocable share of the LLCs’ and LP’s interest expense during the years 2009–2012 because the taxpayer’s father had ample investment income during those years.) Midway through 2011, the taxpayer’s father gave a portion of his membership interests in the LLCs to his taxpayer-son. Then, in October of 2012, the taxpayer’s father died bequeathing his partnership interests in the LP and FLP to his taxpayer-son. The foregoing transfers from the father to the taxpayer-son were treated as part-sale/part-gift transactions because the father’s allocable share of the LLCs’ and LP’s debt (including debt allocated via the FLP) was treated as an amount realized by the father, and an amount paid by the taxpayer-son, under Regulation section 1.752-1(h) and section 1.1001-2(a)(4)(v). In fact, the taxpayer’s father had reported taxable capital gains of approximately $23 million from his “gift” of the LLC interests to his taxpayer-son in 2011. (Presumably, no capital gains were realized or recognized upon the taxpayer father’s bequest of the LP and FLP interests to his taxpayer-son in 2012 due to the estate’s stepped-up basis.)

After receiving the foregoing LLC, LP, and FLP interests, the taxpayer-son did not continue to report his allocable share of the LLCs’ and LP’s interest expense as investment interest. Rather, the taxpayer-son reported his allocable share of the LLCs’ and LP’s interest expense for the years 2012 and 2013 as properly allocable to the underlying real estate assets and rental income of the LLCs and the LP. Accordingly, the taxpayer-son deducted his allocable shares of the interest expense against his allocable shares of the rental income. The Service, noticing the change in treatment of the interest, audited the taxpayer-son (because the LLCs and the LP were not subject to TEFRA-partnership audit rules), disallowed the deduction of the interest expense against the rental income of the LLCs and the LP, and proposed deficiencies for 2012 and 2013 totaling approximately $500,000. (Presumably, unlike his father, the taxpayer-son did not have sufficient investment income to be able to fully deduct his allocable share of the interest expense from the LLCs and LP.)

In support of his position that the interest expense was properly allocable to and deductible against the rental income of the LLCs and the LP (including debt allocated via the FLP), the taxpayer-son relied upon Regulation section 1.752-1(h) and section 1.1001-2(a)(4)(v) cited above as well as the Regulations under section 163. Specifically, Temporary Regulation section 1.163-8T(c)(3)(ii)(C) provides that if a taxpayer “takes property subject to debt,” and no debt proceeds are disbursed to the taxpayer, the debt is treated as being used to acquire the property. Accordingly, the associated interest expense is allocated to the acquired property for purposes of the deduction limitations of section 163. The taxpayer-son contended that even though his LLC interests were received via a “gift,” and the LP interest was received via a bequest, the taxpayer-son was allocated a share of LLCs’ and the LP’s debt, and he thus acquired his interests “subject to debt.” Further, the taxpayer-son relied upon Notice 89-35, which provides in relevant part that:

In the case of debt proceeds allocated under section 1.163-8T to the purchase of an interest in a passthrough entity (other than by way of a contribution to the capital of the entity), the debt proceeds and the associated interest expense shall be allocated among all the assets of the entity using any reasonable method.

The Service argued that the taxpayer-son was bound by the father’s treatment of the interest as an investment expense because a “once investment interest, always investment interest” rule should apply. Moreover, the Service argued that Temporary Regulation section 1.163-8T(c)(3)(ii)(C) was not relevant because the taxpayer-son did not actually take his LLC and LP interests “subject to a debt” as contemplated by the Regulations and Notice 89-35; rather, the rules of Regulation section 1.752-1(h) and section 1.1001-2(a)(4)(v) use such an approach for purposes of Subchapter K, not section 163.

The Tax Court (Judge Lauber) disagreed with the Service, citing Temporary Regulation section 1.163-8T(c)(3)(ii)(C) and Notice 89-35, as noted above. Judge Lauber determined that the Service’s position had no authoritative support and that the taxpayer-son’s position was correct. Judge Lauber wrote “[i]n short, whereas [the taxpayer’s father] received a debt-financed distribution, [the taxpayer-son] is treated as having made a debt-financed acquisition of the partnership interests he acquired from [his father].” Therefore, reasoned Judge Lauber, the Service’s own Notice 89-35 expressly allows the interest expense to be allocated to the real estate assets and income generated by the LLCs and LP (as was done by the taxpayer-son).

D. Section 121

There were no significant developments regarding this topic during 2019.

E. Section 1031

There were no significant developments regarding this topic during 2019.

F. Section 1033

There were no significant developments regarding this topic during 2019.

G. Section 1035

There were no significant developments regarding this topic during 2019.

H. Miscellaneous

1. No depositors, no regulation, no “bank,” no bad debt deduction for worthless asset-backed securities. An otherwise profitable victim of the financial meltdown can’t deduct any losses over $500,000,000 on asset-back securities. This one ain’t funny.

In MoneyGram International, Inc. v. Commissioner, MoneyGram’s core business was to provide consumers and financial institutions with payment services that involve the movement of money through three main channels: money transfers, money orders, and payment processing services. MoneyGram derived its revenue from the transaction fees paid by its customers and from management of currency exchange spreads on international money transfers. When a customer purchased a money order by giving cash to a MoneyGram agent, the agent had to remit the funds to MoneyGram immediately. However, MoneyGram typically entered into agreements with its agents allowing them to retain and use the funds for an agreed-upon period. MoneyGram also derived revenue from the temporary investment of funds remitted from its financial institution customers until such time as the official checks and money orders cleared. MoneyGram was not subject to regulation as a bank, and it had never been regulated as a bank by any federal banking regulator. On its 2007 and 2008 Forms 1120, MoneyGram classified its business as “nondepository credit intermediation.”

During 2007 and 2008, MoneyGram undertook a recapitalization that included writing down or writing off a substantial volume of partially or wholly worthless securities. MoneyGram claimed ordinary section 166(a) bad debt deductions with respect to the partial or complete worthlessness of hundreds of millions of dollars of non-REMIC, asset-backed securities in which it had invested. (Treating these losses as capital losses would have generated no current tax benefit for MoneyGram because it had no capital gain net income during 2007 and 2008 against which the capital losses could be offset.) The Service determined that the securities were “debts evidenced by a security” under section 165(g)(2)(C), that MoneyGram was entitled to ordinary bad debt deductions (via section 582(a)), as opposed to capital losses, but only if it were a “bank” within the meaning of section 581, and that MoneyGram was not a “bank;” thus, the Service disallowed the bad debt deductions.

The Tax Court (Judge Lauber) upheld the deficiency. To qualify as a “bank” under section 581, a taxpayer must satisfy three distinct requirements.

First, it must be “a bank or trust company incorporated and doing business” under Federal or State law. Second, “a substantial part” of [its] business must “consist[] of receiving deposits and making loans and discounts.” Third, [it] must be “subject by law to supervision and examination” by Federal or State authorities having supervision over banking institutions.

Under this test, during 2007 and 2008 MoneyGram did not qualify as a “bank” because it did not display the essential characteristics of a bank as that term is commonly understood and because a substantial part of its business did not consist of receiving bank deposits or making bank loans. Because MoneyGram was not a “bank” within the meaning of section 581, it was ineligible to claim ordinary loss deductions on account of the worthlessness of its securities under section 582. The losses were capital losses.

a. Maybe MoneyGram is a bank. The Fifth Circuit reversed and remanded for consideration whether MoneyGram was receiving “deposits” and whether it was making “loans and discounts.” In a per curiam opinion, the Court of Appeals for the Fifth Circuit vacated the Tax Court’s decision and remanded for further proceedings. One requirement to qualify as a “bank” under section 581 is that “a substantial part” of the taxpayer’s business must “consist[] of receiving deposits and making loans and discounts.” Section 581 does not define the terms “deposits” or “loans.” The Tax Court held that the term “deposits” as used in section 581 means “funds that customers place in a bank for the purpose of safekeeping,” that are “repayable to the depositor on demand or at a fixed time,” and which are held “for extended periods of time.” The Tax Court concluded that the funds received by MoneyGram in exchange for issuing money orders and the funds received from its financial institution customers were not “deposits” because MoneyGram did not hold these funds for safekeeping or for an extended period of time. The Tax Court also held that a “loan” as that term is used in section 581 “is memorialized by a loan instrument, is repayable with interest, and generally has a fixed (and often lengthy) repayment period.” The Tax Court concluded that the funds MoneyGram permitted its agents to keep temporarily, which were reflected on MoneyGram’s books as accounts receivable, were not loans but merely accounts receivable typical of any business that provides goods or services.

The Fifth Circuit disagreed with the definitions the Tax Court assigned to the terms “deposits” and “loans.” With respect to the term “deposits,” the Fifth Circuit held that the Tax Court had erred by interpreting it to require that MoneyGram hold funds received “for an extended period of time.” With respect to the term “loans,” the Fifth Circuit disagreed entirely with the definition used by the Tax Court. According to the Fifth Circuit, the “central inquiry” for determining if a transaction is a loan for tax purposes is whether the parties intend that the money advanced be repaid. The Fifth Circuit noted that it has adopted a non-exhaustive, seven-factor test to determine whether the parties to a transaction intended an arrangement to be a loan. Finally, the Fifth Circuit observed that section 581 requires as a condition of “bank” status that the taxpayer make loans and discounts. The Tax Court had not addressed whether MoneyGram made discounts. Because the Tax Court had applied incorrect definitions of the terms “deposits” and “loans” and had not addressed whether MoneyGram made “discounts,” the Fifth Circuit reversed the Tax Court and remanded for reconsideration.

b. We got it right the first time, says the Tax Court. MoneyGram is not a bank. On remand, in a lengthy opinion by Judge Lauber, the Tax Court concluded that MoneyGram neither received deposits nor made loans. The court also concluded that MoneyGram did not make discounts. Therefore, the court held, MoneyGram was not a “bank” within the meaning of section 581 and its losses were capital rather than ordinary losses. With respect to the issue whether MoneyGram received deposits, the Tax Court held that MoneyGram did not receive funds “for the purpose of safekeeping.” Although it received funds from its agents who issued money orders and received funds from its financial institution customers (such as banks) in connection with the processing of checks, in neither case, the court held, did MoneyGram receive the funds for the purpose of safekeeping.

The Tax Court also concluded that MoneyGram did not make “loans” when it allowed its agents that issued money orders to keep the funds for short periods of time before remitting them to MoneyGram. The court was influenced in part by the fact that MoneyGram had argued in several cases involving the bankruptcy of its agents that “the agent’s obligation to it arises by operation of law upon the agent’s defalcation as Trustee, not from a debtor-creditor relationship of the sort created by an ordinary secured loan.” Finally, the Tax Court held that MoneyGram did not make discounts. The court described the term “making discounts” in section 581, which provides a definition of “bank” that dates from 1936, as “somewhat old-fashioned terminology.” The term describes a practice more common at that time of a bank customer who held a bill or promissory note who would ask the bank to “discount” the note by paying the customer a lesser amount, say 90 cents on the dollar. The court analyzed MoneyGram’s investments in asset-backed securities and its purchase of commercial paper and concluded that neither activity constituted making discounts within the meaning of section 581.

IV. Compensation Issues

A. Fringe Benefits

1. Ministers pray this “crabby” case gets reversed (again!) on appeal.

In Gaylor v. Mnuchin, a case that had previously been overturned on appeal to the Seventh Circuit, the District Court for the Western District of Wisconsin (Judge Crabb) held section 107(2) to be unconstitutional because it violates the First Amendment’s establishment clause. Section 107(2) excludes from gross income a “rental allowance” paid to a minister as part of his or her compensation. Section 107(1) excludes the “rental value of a home” furnished to a minister as part of his or her compensation. For technical reasons, only section 107(2)’s “rental allowance” exclusion was at issue in the case. The named plaintiff, Gaylor, is co-president of the true plaintiff, Freedom from Religion Foundation, Inc. (FFRF).

In a prior iteration of the case, Freedom from Religion Foundation, Inc. v. Lew, the Court of Appeals for the Seventh Circuit vacated Judge Crabb’s prior ruling striking down section 107(2) by determining that FFRF lacked standing to sue; however, the Seventh Circuit essentially instructed FFRF on how it might obtain standing. FFRF dutifully followed the Seventh Circuit’s directions and then refiled its establishment clause claim with Judge Crabb. FFRF argued that section 107(2) violates the establishment clause because it “demonstrate[s] a preference for ministers over secular employees.” Judge Crabb agreed and ruled that section 107(2) is unconstitutional and ordered the Service to cease enforcing the statute. In a subsequent decision, Judge Crabb ordered that the court’s injunction prohibiting enforcement of the statute be stayed until 180 days after resolution of any appeal. In other words, stay tuned . . . .

a. Prayers answered! On appeal, the Seventh Circuit reversed and upheld the constitutionality of section 107(2). The Treasury Department and the Service argued before the Seventh Circuit that, although section 107(2) seems to advance a religious purpose by excluding rental allowances paid to “ministers of the gospel,” the history of section 107(2) reveals a secular purpose. To wit, Congress enacted section 107 in 1923 as a response to the Service’s original position in 1921 that the “convenience of the employer” exception for employer-providing housing (now codified at section 119(a)(2)) did not apply to ministers. The Treasury Department and the Service argued that section 107(2) was merely an extension of the “convenience of the employer” exception to gross income, not an impermissible government “establishment” of a religious preference. Writing for the court, Judge Brennan agreed, stating:

Reading § 107(2) in isolation from the other convenience-of-the-employer provisions, and then highlighting the term “minister,” could make the challenged statute appear to provide a government benefit exclusively to the religious. But reading it in context, as we must, we see § 107(2) is simply one of many per se rules that provide a tax exemption to employees with work-related housing requirements.

Moreover, Judge Brennan explained that although section 107(2) has broader application than the “convenience of the employer” exception of section 119(a)(2), the breadth of section 107(2) does not render the statute unconstitutional. In fact, Judge Brennan reasoned that section 107(2) is broadly written to avoid excessive government entanglement with the internal operations of a church. Otherwise, without section 107(2), section 119(a)(2) would require the Service to interrogate ministers as to the use of their homes for religious purposes. Further, section 119(a)(2) would require the Service to determine the scope of the “business” of the church and where and how far the “premises” of the church extend. As written, section 107(2) avoids such excessive entanglement of government into the affairs of the church. Similarly, the court determined that section 107(2) does not unconstitutionally “advance” religion over secular purposes because providing a tax exemption does not “connote[] sponsorship, financial support, and active involvement of the [government] in religious activity.” Finally, the court ruled that section 107(2) passes the “historical significance” test under the establishment clause because tax exemptions have been provided to religious and religious-affiliated organizations by Congress almost since the Sixteenth Amendment authorized the federal income tax in 1913.

2. Service Chief Counsel says that an individual who is a 2-percent S corporation shareholder pursuant to the section 318 constructive ownership rules is entitled to a deduction under section 162(l) for amounts paid by the S corporation under a group health plan for all employees and included in the individual’s gross income if the individual otherwise meets the requirements of section 162(l).

In Chief Counsel Advice 2019-12-001, the Service Office of Chief Counsel concluded that an individual who was treated as a 2-percent S corporation shareholder—because the stock of a family member was attributed to the individual under the constructive ownership rules of section 318—could deduct the amounts paid by the S corporation under a group health plan and included in the individual’s gross income.

a. Background. Under section 1372(a), an S corporation is treated as a partnership and a 2-percent shareholder of an S corporation is treated as a partner for purposes of applying the provisions of the Code relating to employee fringe benefits. For this purpose, a “2-percent shareholder” is any person who owns (or is considered to own under the constructive ownership rules of section 318) on any day during the S corporation’s tax year more than two percent of the corporation’s outstanding stock or stock possessing more than two percent of the total combined voting power of all stock of the corporation. According to Revenue Ruling 91-26, accident and health insurance premiums paid by an S corporation on behalf of a 2-percent shareholder-employee as compensation for services are treated like guaranteed payments to partners under section 707(c). Therefore, the S corporation can deduct the premiums and the 2-percent shareholder-employee must include an appropriate portion of the premiums in gross income. The S corporation must report the premiums on the 2-percent shareholder-employee’s Form W-2, but according to Service Announcement 92-16, such amounts are not wages subject to Social Security and Medicare taxes if the requirements of the exclusion in section 3121(a)(2)(B) are met. Section 162(l) authorizes an above-the-line deduction for a taxpayer who is an employee within the meaning of section 401(c)(1) for an amount equal to the amount paid during the year for insurance that constitutes medical care for the taxpayer and the taxpayer’s spouse, dependents, and children who have not attained the age of 27. This deduction is available to a 2-percent shareholder-employee of an S corporation if the plan is established by the S corporation. The deduction is limited to the taxpayer’s earned income from the trade or business with respect to which the plan providing medical care is established and is not available if the taxpayer is eligible to participate in a subsidized health plan maintained by an employer of the taxpayer or of the taxpayer’s spouse or dependents.

b. Facts. An individual owned 100% of an S corporation, which employed the individual’s family member. Because of the family relationship, the family member was considered to be a 2-percent shareholder pursuant to the attribution of ownership rules under section 318. The S corporation provided a group health plan for all employees, and the amounts paid by the S corporation under the group health plan were included in the family member’s gross income. Chief Counsel was asked whether an individual who was a 2-percent shareholder of an S corporation pursuant to the constructive ownership rules of section 318 by virtue of being a family member of the S corporation’s sole shareholder was entitled to the deduction under section 162(l) for amounts that were paid by the S corporation under a group health plan for all employees and included in the individual’s gross income.

c. Chief Counsel’s Conclusion. Chief Counsel concluded that:

[A]n individual who is a 2-percent shareholder of an S corporation pursuant to the attribution of ownership rules under § 318 is entitled to the deduction under § 162(l) for amounts that are paid by the S corporation under a group health plan for all employees and included in the individual’s gross income if the individual otherwise meets the requirements of section 162(l).

B. Qualified Deferred Compensation Plans

1. They were just kidding! Treasury and the Service no longer plan to amend the Regulations under section 401(a)(9) to prohibit giving retirees receiving annuity payments the option to receive a lump-sum payment.

A number of sponsors of defined benefit plans have amended their plans to provide a limited period during which certain retirees who are currently receiving lifetime annuity payments from those plans may elect to convert their annuities into lump sums that are payable immediately. These arrangements are sometimes referred to as retiree lump-sum windows. In Notice 2015-49, the Service announced that the Treasury Department and the Service planned to amend the required minimum distribution Regulations under section 401(a)(9) to provide that qualified defined benefit plans generally are not permitted to replace any joint and survivor, single life, or other annuity currently being paid with a lump-sum payment or other accelerated form of distribution. With certain exceptions, the amendments to the Regulations were to apply as of July 9, 2015.

Notice 2019-18 provides that the Treasury Department and the Service no longer intend to propose the amendments to the Regulations under section 401(a)(9) that were described in Notice 2015-49. The Notice indicates that the Treasury Department and the Service will continue to study the issue of retiree lump-sum windows. The Notice further provides:

Until further guidance is issued, the IRS will not assert that a plan amendment providing for a retiree lump-sum window program causes the plan to violate § 401(a)(9), but will continue to evaluate whether the plan, as amended, satisfies the requirements of §§ 401(a)(4), 411, 415, 417, 436, and other sections of the Code. During this period, the IRS will not issue private letter rulings with regard to retiree lump-sum windows. However, if a taxpayer is eligible to apply for and receive a determination letter, the IRS will no longer include a caveat expressing no opinion regarding the tax consequences of such a window in the letter.

2. Some inflation-adjusted numbers for 2020.

Elective deferrals in sections 401(k), 403(b), and 457 plans are increased from $19,000 to $19,500 with a catch-up provision for employees aged 50 or older that is increased from $6,000 to $6,500.

The limit on contributions to an IRA remains unchanged at $6,000. The AGI phase-out range for contributions to a traditional IRA by employees covered by a workplace retirement plan is increased to $65,000–$75,000 (from $64,000–$74,000) for single filers and heads of household, increased to $104,000–$124,000 (from $103,000–$123,000) for married couples filing jointly in which the spouse who makes the IRA contribution is covered by a workplace retirement plan, and increased to $189,000–$199,000 (from $193,000–$203,000) for an IRA contributor who is not covered by a workplace retirement plan and is married to someone who is covered. The phase-out range for contributions to a Roth IRA is increased to $196,000–$206,000 (from $193,000–$203,000) for married couples filing jointly, and increased to $124,000–$139,000 (from $122,000–$137,000) for singles and heads of household.

The annual benefit from a defined benefit plan under section 415 is increased to $230,000 (from $225,000).

The limit for defined contribution plans is increased to $57,000 (from $56,000).

The amount of compensation that may be taken into account for various plans is increased to $285,000 (from $280,000), and is increased to $425,000 (from $415,000) for government plans.

The AGI limit for the retirement savings contribution credit for low- and moderate-income workers is increased to $65,000 (from $64,000) for married couples filing jointly, increased to $48,750 (from $48,000) for heads of household, and increased to $32,500 (from $32,000) for singles and married individuals filing separately.

3. Proposed Regulations provide guidance under section 401 relating to new life expectancy and distribution period tables used to calculate minimum distributions from qualified plans, IRAs, and annuities.

The Treasury Department and the Service have issued Proposed Regulations that provide guidance on the use of updated life expectancy and distribution period tables under Regulation section 1.401(a)(9)-9. In general, the Proposed Regulations seek to update the existing tables using current mortality data based on mortality rates for 2021. The new tables allow for longer life expectancies than the current tables under the existing Regulations and generally result in a reduction of required minimum distributions. In turn, this allows for retention of larger amounts in retirement accounts in contemplation of participants having slightly longer lives.

The updated life expectancy and distribution period tables are proposed to apply to distributions on or after January 1, 2021. Thus, for an individual who attains the age at which required minimum distributions must begin in 2020, the Proposed Regulations would not apply to the distribution for the 2020 calendar year (which is due by April 1, 2021). The Proposed Regulations would apply to the required minimum distribution for the individual’s 2021 calendar year, which is due by December 31, 2021. As an aside, while the Proposed Regulations indicate age 70½ as the age at which required minimum distributions must begin, the authors note that section 114 of the Setting Every Community Up for Retirement Enhancement Act of 2019 (SECURE Act) amended section 401(a)(9)(C)(i)(I) to increase the age at which required minimum distributions must begin to 72. Presumably, these Proposed Regulations will be amended to reflect this change.

The Proposed Regulations also include a transition rule that applies under certain circumstances if an employee dies prior to January 1, 2021. The transition rule applies in three situations: (1) the employee dies before the required beginning date with a non-spousal designated beneficiary, (2) the employee dies after the required beginning date without a designated beneficiary, and (3) the employee, who is younger than the designated beneficiary, dies after the required beginning date. Under these circumstances, a set of specific rules applies in relation to the distribution period for calendar years following the calendar year of the employee’s death.

4. The cap on elective deferrals to section 401(k) plans pursuant to automatic contribution arrangements is now 15%.

Section 102 of the SECURE Act amended section 401(k)(13)(C)(iii) to increase the cap on elective deferrals to a section 401(k) plan under an automatic contribution arrangement from 10% to 15%. An automatic contribution arrangement allows an employer automatically to deduct elective deferrals from an employee’s wages unless the employee makes an election not to contribute or to contribute a different amount. This change applies to plan years beginning after December 31, 2019.

5. Congress has increased the age at which RMDs must begin to 72.

Section 114 of the SECURE Act amended section 401(a)(9)(C)(i)(I) to increase the age at which required minimum distributions (RMDs) from a qualified plan (including IRAs) must begin from 70½ to 72. Pursuant to this amendment, RMDs must begin by April 1 of the calendar year following the later of the calendar year in which the employee attains age 72 or, in the case of an employer plan, the calendar year in which the employee retires. This latter portion of the rule allowing deferral of RMDs from employer plans until retirement does not apply to a five-percent owner (as defined in section 416). The increase in the age at which RMDs must begin until age 72 applies to distributions required to be made after December 31, 2019, with respect to individuals who attain age 70½ after such date.

6. No more stretching out RMDs from non-spousal inherited qualified retirement accounts.

Section 401 of the SECURE Act amended section 401(a)(9)(E) to modify the required minimum distribution (RMD) rules for inherited retirement accounts (defined contribution plans and IRAs). The amendments require all funds to be distributed by the end of the tenth calendar year following the year of death. There is no requirement to withdraw any minimum amount before that date. The current rules, which permit taking RMDs over many years, continue to apply to a designated beneficiary who is (1) a surviving spouse, (2) a child of the participant who has not reached the age of majority, (3) disabled within the meaning of section 72(m)(7), (4) chronically-ill within the meaning of section 7702B(c)(2) with some modifications, or (5) an individual not in any of the preceding categories who is not more than ten years younger than the deceased individual. These changes generally apply to distributions with respect to those who die after December 31, 2019.

7. Penalty-free withdrawals for birth or adoption.

Section 113 of the SECURE Act amended section 72(t)(2) to add new section 72(t)(2)(H), which provides for penalty-free withdrawals from “applicable eligible retirement plans” for a “qualified birth or adoption distribution.” A “qualified birth or adoption distribution” is defined as “any distribution from an applicable eligible retirement plan to an individual if made during the one-year period beginning on the date on which a child of the individual is born or on which the legal adoption by the individual of an eligible adoptee is finalized.” A distribution can be treated as qualifying only if the taxpayer includes the name, age, and taxpayer identification number of the child on the taxpayer’s tax return for the taxable year. The maximum penalty-free distribution is $5,000 per individual per birth or adoption. This change applies to distributions made after Dec. 31, 2019.

8. “Difficulty of care” payments that are excluded from gross income are now treated as compensation for purposes of contributing to defined contribution plans and IRAs.

Section 116 of the SECURE Act amended section 408(o) to add new section 408(o)(5) and amended section 415(c) to add new section 415(c)(8). These provisions allow taxpayers receiving “difficulty of care payments” that are excludable from gross income under section 131 to treat such payments as compensation for purposes of the limits on contributing to a defined contribution plan or IRA. Generally, difficulty of care payments are defined in section 131(c)(1) as compensation for providing additional care to a qualified foster individual that is required by reason of the individual’s physical, mental, or emotional handicap and that is provided in the home of the foster care provider. This change applies to contributions to IRAs after December 20, 2019, the date of enactment, and applies to defined contribution plans for plan years beginning after December 31, 2015.

In Feigh v. Commissioner, the Tax Court held that, although Notice 2014-7 treats Medicaid waiver payments as difficulty of care payments that are excludable from gross income under section 131, such payments are earned income for purposes of the earned income credit and the child tax credit. Generally, Medicaid waiver payments are payments made by a state that has obtained a Medicaid waiver that allows the state to include in the state’s Medicaid program the cost of home or community-based services (other than room and board) provided to individuals who otherwise would require care in a hospital, nursing facility, or intermediate care facility. The legislative changes made by the SECURE Act do not alter the result in Feigh.

9. Loans from qualified employer plans are treated as taxable distributions if they are made through the use of credit cards or similar arrangements.

Section 108 of the SECURE Act amended section 72(p)(2) to redesignate section 72(p)(2)(D) as section 72(p)(2)(E) and to add new section 72(p)(2)(D), which provides an additional requirement for a loan from a qualified employer plan to avoid being treated as a taxable distribution. Under section 72(p)(1), a loan from a qualified employer plan is treated as a distribution unless it meets certain requirements set forth in section 72(p)(2). One requirement (provided in section 72(p)(2)(A)) is that the loan must not exceed the lesser of (1) $50,000 or (2) the greater of one-half of the present value of the employee’s nonforfeitable accrued benefit or $10,000. A second requirement (provided in section 72(p)(2)(B)) is that the loan must be repaid within five years. A third requirement (provided in section 72(p)(2)(C)) is that substantially level amortization of the loan (with payments not less frequently than quarterly) must take place over the term of the loan. New section 72(p)(2)(D) provides a fourth requirement, which is that the loan must not be “made through the use of any credit card or any other similar arrangement.” This requirement applies to loans made after December 20, 2019, the date of enactment.

10. Congress has made access to retirement plan funds easier for survivors of certain natural disasters.

Section 202 of the Taxpayer Certainty and Disaster Tax Relief Act of 2019 provides special rules that apply to distributions from qualified employer plans and IRAs and to loans from qualified employer plans for survivors of certain natural disasters.

a. Qualified Disaster Distributions. A “qualified disaster distribution” is defined as any distribution from an eligible retirement plan as defined in section 402(c)(8)(B) (which includes qualified employer plans and IRAs) that was made: (1) before June 17, 2020 (the date that is 180 days after December 20, 2019, the date of enactment of the legislation), (2) on or after the first day of the incident period of a qualified disaster, and (3) to an individual whose principal place of abode at any time during the incident period of the qualified disaster was located in the qualified disaster area of that qualified disaster and who sustained an economic loss by reason of that qualified disaster.

Section 202(a) of the legislation provides four special rules for qualified disaster distributions.

1. The legislation provides that qualified disaster distributions up to an aggregate amount of $100,000 for each qualified disaster are not subject to the normal ten-percent additional tax of section 72(t) that applies to distributions to a taxpayer who has not reached age 59½.

2. The legislation provides that, unless the taxpayer elects otherwise, any income resulting from a qualified disaster distribution is reported ratably over the three-year period beginning with the year of the distribution.

3. The legislation permits the recipient of a qualified disaster distribution to contribute up to the amount of the distribution to a qualified employer plan or IRA that would be eligible to receive a rollover contribution of the distribution. The contribution need not be made to the same plan from which the distribution was received but must be made during the three-year period beginning on the day after the date on which the distribution was received. If contributed within the required three-year period, the distribution and contribution are treated as made in a direct trustee-to-trustee transfer within 60 days of the distribution. The apparent intent of this rule is to permit the taxpayer to exclude the distribution from gross income to the extent it is recontributed within the required period. Because the recontribution might take place in a later tax year than the distribution, presumably a taxpayer would include the distribution in gross income in the year received and then file an amended return for the distribution year upon making the recontribution.

4. Qualified disaster distributions are not treated as eligible rollover distributions for purposes of the withholding rules and, therefore, are not subject to the normal 20% withholding that applies to eligible rollover distributions under section 3405(c).

b. Recontributions of Withdrawals Made for Home Purchases. Section 202(b) of the legislation permits an individual who received a “qualified distribution” to contribute up to the amount of the distribution to a qualified employer plan or IRA that would be eligible to receive a rollover contribution of the distribution. A qualified distribution is a hardship distribution that an individual received from a qualified employer plan or IRA during the period that is 180 days before the first day of the incident period of the relevant qualified disaster and ending on the date that is 30 days after the last day of the incident period that was to be used to purchase or construct a principal residence in a qualified disaster area that was not purchased or constructed on account of the qualified disaster. The contribution need not be made to the same plan from which the distribution was received but must be made during the “applicable period,” which is the period beginning on the first day of the incident period of the qualified disaster and ending on the date that is 30 days after the last day of the incident period. The distribution and contribution are treated as made in a direct trustee-to-trustee transfer within 60 days of the distribution. The apparent intent of this rule is to permit the taxpayer to exclude the distribution from gross income to the extent it is recontributed within the required period.

c. Loans. For qualified individuals, section 202(c) of the legislation increases the limit on loans from qualified employer plans and permits repayment over a longer period of time. Normally, under section 72(p), a loan from a qualified employer plan is treated as a distribution unless it meets certain requirements. One requirement is that the loan must not exceed the lesser of (1) $50,000 or (2) the greater of one-half of the present value of the employee’s nonforfeitable accrued benefit or $10,000. A second requirement is that the loan must be repaid within five years. In the case of a loan made to a “qualified individual” during the period from December 20, 2019 (the date of enactment) through June 16, 2020 (the 180-day period beginning on the date of enactment), the legislation increases the limit on loans to the lesser of (1) $100,000 or (2) the greater of all of the present value of the employee’s nonforfeitable accrued benefit or $10,000.

The legislation also provides that, if a qualified individual has an outstanding plan loan on the first day of the incident period of a qualified disaster with a due date for any repayment occurring during the period beginning on the first day of the incident period and ending on the date which is 180 days after the last day of the incident period, then the due date is delayed for one year. If an individual takes advantage of this delay, then any subsequent repayments are adjusted to reflect the delay in payment and interest accruing during the delay. This appears to require reamortization of the loan.

A “qualified individual” is defined as an individual whose principal place of abode at any time during the incident period of a qualified disaster is located in the qualified disaster area with respect to that qualified disaster and who sustained an economic loss by reason of the qualified disaster.

d. Defined Terms. Several key terms are defined in section 201 of the Taxpayer Certainty and Disaster Tax Relief Act of 2019. These are as follows:

(i) The term “incident period” with respect to any qualified disaster is the period specified by FEMA as the period during which the disaster occurred, except that the period cannot be treated as beginning before January 1, 2018, or ending after January 19, 2020 (the date that is 30 days after the date of enactment of the legislation).

(ii) The term “qualified disaster zone” is the portion of the qualified disaster area determined by the President to warrant individual or individual and public assistance from the federal government under the Robert T. Stafford Disaster Relief and Emergency Assistance Act by reason of the qualified disaster with respect to the qualified disaster area.

(iii) The term “qualified disaster area” is an area with respect to which the President declared a major disaster from January 1, 2018, through February 18, 2020 (the date that is 60 days after the date of enactment of the legislation), under section 401 of the Stafford Act if the incident period of the disaster began on or before December 20, 2019 (the date of enactment). To avoid providing double benefits, the legislation excludes the California wildfire disaster area, for which similar relief was provided by the Bipartisan Budget Act of 2018.

(iv) “The term ‘qualified disaster’ means, with respect to any qualified disaster area, the disaster by reason of which a major disaster was declared with respect to such area.”

C. Nonqualified Deferred Compensation, Section 83, and Stock Options

There were no significant developments regarding this topic during 2019.

D. Individual Retirement Accounts

1. A rollover that was deposited 62 days after withdrawal from an IRA was not taxable because it constituted a bookkeeping error and qualified for a hardship waiver.

In Burack v. Commissioner, the taxpayer withdrew $524,981 from her IRA to purchase a home while waiting for her former home to sell. She planned to redeposit the funds in her IRA within the 60-day period permitted by section 408(d)(3)(A) for making a tax-free rollover of IRA funds. Pershing, LLC served as custodian of the IRA. The taxpayer’s financial adviser was a representative of Capital Guardian, LLC. The relationship between Pershing and Capital Guardian was not entirely clear. Capital Guardian generated statements for the taxpayer’s IRA and the statements listed both Pershing and Capital Guardian.

Pursuant to instructions from Capital Guardian, on Thursday, August 21, 2014, 57 days after the taxpayer’s withdrawal, the taxpayer sent a check for $524,981 by overnight delivery to Capital Guardian, which received the check the next day. For reasons that are not clear, the check was not deposited at Pershing in the taxpayer’s IRA until Tuesday, August 26, 2014, which was 62 days after the taxpayer’s withdrawal. The Service issued a notice of deficiency in which the Service asserted that the taxpayer had to include the withdrawn funds in gross income because the taxpayer had not rolled them over within the required 60-day period.

The Tax Court (Judge Ruwe) held that the taxpayer was entitled to treat the transaction as a tax-free rollover for two reasons. The court first concluded that the withdrawn funds were not redeposited in a timely manner because of a bookkeeping error by Capital Guardian, stating that “[b]ecause the check was received by Capital Guardian during the rollover period but not book-entered by Capital Guardian until after, we find that the late recording is due to a bookkeeping error.” The court reasoned that the situation was analogous to that in Wood v. Commissioner, in which the court reached a similar conclusion when the taxpayer had transferred stock to Merrill Lynch within the 60-day period with instructions that it be deposited in the taxpayer’s IRA, but Merrill Lynch deposited the stock in a nonqualified account before transferring it to the IRA after the 60-day period.

The court then held that the taxpayer was eligible for a hardship waiver under section 408(d)(3)(I). An automatic waiver under section 408(d)(3)(I) is granted if, prior to the expiration of the 60-day period, a financial institution receives funds on behalf of a taxpayer, the taxpayer follows all procedures required by the financial institution for depositing the funds into an eligible retirement plan (including giving instructions for deposit of the funds), and “solely due to an error on the part of the financial institution, the funds are not deposited into an eligible retirement plan within the 60-day rollover period” provided two further conditions are satisfied: (1) the funds are deposited into an eligible retirement plan within one year from the beginning of the 60-day rollover period and (2) a valid rollover would have occurred if the financial institution had deposited the funds as instructed. The court concluded that all requirements for an automatic hardship waiver had been satisfied and that this served as an alternative basis for treating the taxpayer’s withdrawal and contribution as a tax-free rollover.

2. Amounts paid to an individual to aid in the pursuit of graduate or postdoctoral study and included in the individual’s gross income are now treated as compensation for purposes of contributing to an IRA.

Section 106 of the SECURE Act amended section 219(f)(1) to provide that amounts paid to an individual to aid in the pursuit of graduate or postdoctoral study and included in the individual’s gross income are now treated as compensation for purposes of the limit on contributing to an IRA. Such amounts include taxable stipends and non-tuition fellowship payments received by graduate and postdoctoral students. This change applies to taxable years beginning after December 31, 2019.

3. ♪♫ I don’t know, but I’ve been told, if you [contribute to an IRA] you’ll never grow old. ♫♪ Congress has eliminated the age restriction for contributions to traditional IRAs.

Section 107 of the SECURE Act repealed former section 219(d)(1). The effect of this change is to eliminate the age restriction (age 70½ for contributions to traditional IRAs). The legislation also amends section 408(d)(8)(A), which allows taxpayers who are age 70½ or older to make tax-free distributions to a charity from an IRA of up to $100,000 per year, to reduce a taxpayer’s ability to make such tax-free distributions to a charity by the amount of deductible IRA contributions made after age 70½. The reduction in the $100,000 annual limit under section 408(d)(8)(A) is the amount by which the taxpayer’s aggregate deductible contributions to an IRA made after age 70½ exceed the aggregate reductions of the $100,000 limit in all prior taxable years. These changes apply to contributions and distributions made for taxable years beginning after December 31, 2019.

V. Personal Income and Deductions

A. Rates

1. Do we want kids to be entrepreneurial, or don’t we? Congress has repealed the 2017 modification of the kiddie tax, which had applied the rates of tax applicable to trusts and estates to the unearned income of children.

Section 501 of the SECURE Act repealed section 1(j)(4). Section 1(j)(4) had been added to the Code by section 11001(a) of the TCJA. For taxable years beginning after 2017 and before 2026, section 1(j)(4) modified the so-called “kiddie tax” by taxing the unearned income of children under the rate schedule that applies to trusts and estates. (The earned income of children continued to be taxed at the rates that normally apply to a single individual.) This changed the approach of prior law, under which the tax on unearned income of children was determined by adding it to the income of the child’s parents and calculating a hypothetical increase in tax for the parents. Under the approach of former section 1(j)(4), the child’s tax on unearned income was unaffected by the parents’ tax situation. The TCJA did not change the categories of children subject to the kiddie tax. Congress has now repealed section 1(j)(4), which means that the regime in effect prior to the TCJA, reflected in section 1(g), now is back in effect.

Congress also amended section 55(d)(4)(A) by adding section 55(d)(4)(A)(iii), which provides that, for purposes of the alternative minimum tax, subsection (j) of section 59 shall not apply. The effect of this amendment is to make inapplicable the limitation on the AMT exemption amount of a child to whom the kiddie tax applies.

The repeal of former section 1(j)(4) generally applies to taxable years beginning after December 31, 2019, but taxpayers can elect, under procedures to be prescribed, for the repeal to apply also to taxable years beginning in 2018 alone, 2019 alone, or both 2018 and 2019. The elimination of the section 59(j) limit on a child’s AMT exemption amount applies to taxable years beginning after December 31, 2017. Amendment of 2018 returns might be necessary.

The provision repealing section 1(j)(4) was an amendment proposed by Congressman Don Beyer of Virginia, a member of the House Ways and Means Committee. A press release he issued indicated that the amendment was designed to prevent (1) children who receive benefits as survivors of members of the military or first responders from being subject to higher rates of tax on their benefits and (2) low-income college students from being subject to higher rates of tax on taxable financial aid they receive.

B. Miscellaneous Income

1. Who would have thought that selling your life insurance policy to a stranger was a good idea anyway?

The TCJA, sections 13520–13522, modified the rules concerning the exclusion of life insurance proceeds upon the death of the insured as well as the determination of basis in a life insurance contract. The modified rules primarily impact the tax treatment of so-called life settlements (where a stranger purchases a life insurance policy on a healthy insured) and viatical settlements (where a stranger purchases a life insurance policy on a terminally-ill insured).

As explained in detail below, amended section 101 now contains a special carve-out to the normal life insurance policy transfer-for-value rules. This special carve-out applies to “reportable policy sales,” which generally will include life-settlement and viatical-settlement transactions. Furthermore, section 13520 added new section 6050Y to impose unique reporting requirements on the transferor and the insurer with respect to “reportable policy sales.” In part, new section 6050Y will require disclosure of “reportable death benefits,” as defined, but essentially meaning death benefits paid on an insurance policy that has been transferred in a “reportable policy sale.”

Finally, section 13521 added a new subsection “(B)” to section 1016(a)(1) to clarify (and reverse the Service’s position in Revenue Ruling 2009-13) that basis in an annuity or life insurance contract includes premiums and other costs paid without reduction for mortality expenses or other reasonable charges incurred under the contract (also known as “cost of insurance”). In Notice 2018-41, the Service announced that it will issue proposed regulations providing guidance concerning the new rules and that otherwise required reporting under section 6050Y will be delayed until after final regulations are published. We commend Notice 2018-41 for careful study by those readers advising clients on life settlement and viatical settlement transactions.

The changes made by TCJA to section 101 and the addition of section 6050Y (which are the focus of the Notice) apply to taxable years beginning after 2017. The amendment adding new section 1016(a)(1)(B) applies retroactively to transactions entered into after August 25, 2009.

a. Some background. Section 101 generally excludes from gross income the proceeds of a life insurance policy payable by reason of the death of the insured. If, however, a life insurance policy is transferred for valuable consideration prior to the death of the insured (i.e., “a transfer for value”), then death benefit proceeds (to the extent they exceed the transferee-owner’s basis in the policy) are includable in gross income by the transferee-owner of the policy upon the insured’s death unless an exception applies. These exceptions provide that, notwithstanding a transfer for value, death benefit proceeds remain excludable if (1) the transferee-owner’s basis in the policy is determined in whole or in part by reference to the transferor’s basis (e.g., a carryover basis transaction) or (2) the transferee-owner is the insured, a partner of the insured, a partnership in which the insured is a partner, or a corporation of which the insured is a shareholder or officer. If a transfer-for-value exception does not apply, then Revenue Ruling 2009-14 sets out the Service’s position that any death benefit payable to the transferee-owner is ordinary income (to the extent it exceeds the transferee-owner’s basis in the policy) while a subsequent sale of the policy by the transferee-owner before the death of the insured can produce capital gain.

b. Why new rules? Life-settlement and viatical-settlement transactions have increased over the last several years. The increase in the estate and gift tax exemption has contributed in part to this market because some previously purchased life insurance policies are no longer needed to pay anticipated estate taxes. Changes to restrictive state laws concerning so-called “stranger-owned” life insurance also have contributed to an increase in these transactions.

In a typical life-settlement transaction, the policyholder, often the individual insured under the life insurance contract, sells his or her life insurance contract to an unrelated person. The consideration paid generally is a lump-sum cash payment that is less than the death benefit on the policy, but more than the amount that would be received by the policyholder upon surrender of the life insurance contract.

The Service previously announced its position regarding the tax treatment of life-settlement transactions in Revenue Ruling 2009-13. Oversimplifying somewhat, Revenue Ruling 2009-13 provides that the seller of a policy in a life-settlement transaction recognizes capital gain except with respect to the “inside buildup” in the policy (e.g., growth in cash surrender value of whole life insurance) over prior premium payments. This latter amount attributable to the inside buildup in the policy is characterized as ordinary income. The Service also took the position in Revenue Ruling 2009-13 that the seller’s basis in a transferred policy must be adjusted downward by the cost of insurance separate from the investment in the contract. As discussed above, TCJA’s addition of new section 1016(a)(1)(B) reverses the Service’s position in this regard.

A viatical settlement, a special type of life-settlement transaction, may involve the sale of a life insurance contract by the owner, but under section 101(g) may not necessarily be taxed like a life settlement transaction. Under a viatical settlement, a policyholder may sell or assign a life insurance contract after the insured has become terminally ill or chronically ill (within the meaning of section 101(g)). If any portion of the death benefit under a life insurance contract on the life of an insured who is terminally ill or chronically ill is sold (through the sale of the life insurance contract) or assigned in a viatical settlement to a “viatical-settlement provider” (as defined), the amount paid for the sale or assignment of that portion is treated as an amount paid under the life insurance contract by reason of the death of the insured (which may be excludable under section 101), rather than gain from the sale or assignment (which generally would not be excludable under section 101 unless a transfer-for-value exception applied). A viatical-settlement provider for purposes of these rules is a person regularly engaged in the trade or business of purchasing, or taking assignments of, life insurance contracts insuring the lives of terminally-ill or chronically-ill individuals provided certain requirements are met.

c. So, what’s in the new rules? Under new section 101(a)(3), the longstanding transfer-for-value exceptions described above do not apply if the transfer of the life insurance policy is a “reportable policy sale.” A reportable policy sale is defined as “the acquisition of an interest in a life insurance contract, directly or indirectly, if the acquirer has no substantial family, business, or financial relationship with the insured apart from the acquirer’s interest in such life insurance contract.” Pursuant to section 101(a)(3)(B), the term “indirectly” as used in this context applies to the acquisition of an interest in a life insurance contract via a partnership, trust, or other entity. Beyond the above statutory language, however, new section 101(a)(3) provides no further guidance as to specifics, such as the “substantial family, business, or financial relationships” (including ownership via partnerships, trusts, or other entities) that exempt an otherwise reportable policy sale from the special inclusion rule of new section 101(a)(3). In effect, then, Notice 2018-41 is the Service’s means of telling insurers and those engaged in life-settlement and viatical-settlement transactions that the Service knows the statutes are unclear and that the guidance necessary to comply with the new rules is forthcoming.

d. Proposed Regulations provide guidance on information reporting obligations under section 6050Y related to reportable policy sales of life insurance contracts and payments of reportable death benefits. The Treasury Department and the Service have issued Proposed Regulations that provide guidance on the information reporting obligations created by section 6050Y related to reportable policy sales of life insurance contracts and payments of reportable death benefits. The Proposed Regulations also provide guidance on the amount of death benefits excluded from gross income under section 101 following a reportable policy sale.

Certain provisions of the Proposed Regulations are proposed to apply to reportable policy sales made and reportable death benefits paid after December 31, 2017. Transition rules apply to reportable policy sales made and reportable death benefits paid before the date on which final regulations are published in the Federal Register. Other provisions of the Proposed Regulations are proposed to apply on and after the date final regulations are published in the Federal Register.

2. “I think, therefore I am.” The taxpayer argued that body and mind are inseparable, but the Tax Court gave effect to the Code’s dualist view of body and mind and held that the damages received by the taxpayer were for emotional distress and therefore included in gross income.

In Doyle v. Commissioner, the taxpayer was employed by a corporation in the technology sector but was fired after he brought to the chief executive officer his concerns about the company’s anticompetitive behavior. Following his termination, the taxpayer couldn’t sleep, couldn’t digest food properly, and had a lot of other health problems. He struggled with chronic headaches, he couldn’t concentrate, and he had neck, shoulder, and back pain. His relationship with his wife suffered, and he believes that he’ll deal with some of these issues for the rest of his life.

The taxpayer and his former employer entered into a settlement agreement that provided for payment of $350,000 of “alleged unpaid wages,” which his employer reported on Form W-2, and also provided for payment of $250,000 “for his alleged emotional distress damages,” which his employer reported on Form 1099-MISC. His former employer paid the $250,000 in two equal installments in 2010 and 2011. The taxpayer’s CPA, who had more than 40 years of experience preparing tax returns, concluded that the $250,000 reported on Forms 1099-MISC were excluded from the taxpayer’s gross income under section 104(a)(2), which excludes from gross income the amount of any damages received on account of personal physical injury or physical sickness. The taxpayer’s returns for 2010 and 2011 each included a Schedule C on which the taxpayer reported income of $125,000, deducted some legal fees, and also deducted an amount for “personal injury” (2010) or “pain and suffering” (2011) in an amount sufficient to zero out the income on Schedule C. The taxpayer also deducted some legal fees for 2010 on Schedule A.

The Tax Court (Judge Holmes) found that the taxpayer’s ailments were the consequence of emotional distress he suffered when he was fired. The Tax Court held that the $250,000 received by the taxpayer was includible in the taxpayer’s gross income pursuant to the language of section 104(a), which provides that “emotional distress shall not be treated as a physical injury or physical sickness.” In reaching this conclusion, the court relied on both its prior decisions (such as Pettit v. Commissioner) and the legislative history of the 1996 amendments to section 104(a), both of which establish that, for purposes of section 104(a), “emotional distress” includes physical symptoms that result from emotional distress, such as insomnia, headaches, and stomach disorders. The court rejected the taxpayer’s argument that his job termination caused stress, and that “one can’t really distinguish symptoms of emotional distress from symptoms of other physical injuries or sicknesses because ‘[p]hysical relates to both the body and mind which are inseparable in a person.’” The court concluded that the taxpayer “may well be right ontologically, but not legally.”

The court also disallowed the deduction of legal fees on Schedule C (but not on Schedule A because the Service had not challenged those) and declined to impose accuracy-related penalties under section 6662(a) because the taxpayer had relied in good faith on the advice of his CPA and also because the Service had not introduced any evidence that the penalties had been “personally approved (in writing) by the immediate supervisor of the individual making such [initial] determination” of the penalty as required by section 6751(b)(1).

a. Tax treatment of the amounts received by the taxpayer for unpaid wages. There apparently was no dispute between the parties that the taxpayer had to include in gross income the $350,000 of “alleged unpaid wages” that his former employer paid and reported on Form W-2 because the court did not separately discuss it. If the taxpayer had suffered a physical injury, however, and if his inability to earn the wages was the result of his physical injury, then he should have been able to exclude the unpaid wages from his gross income under section 104(a)(2) because the exclusion applies to all damages that flow from a physical injury.

b. Taxpayers have prevailed in some cases that are difficult to distinguish. The Tax Court concluded in this case that, if a defendant’s conduct causes a taxpayer to have emotional distress, then the taxpayer cannot exclude from gross income under section 104(a)(2) any damages or settlement payments received because emotional distress is not a physical injury. The court further concluded that this rule applies even if a taxpayer suffers physical symptoms of the emotional distress, such as insomnia or stomach disorders. In some cases, however, the line between a physical injury, on the one hand, and physical symptoms of emotional distress, on the other, has not been entirely clear. For example, in Parkinson v. Commissioner, the Tax Court concluded that a taxpayer who suffered a heart attack as a result of emotional distress that he had experienced in the workplace had suffered a physical injury. Similarly, in Domeny v. Commissioner, the Tax Court held that a taxpayer whose workplace stress resulted in a flare-up of her pre-existing multiple sclerosis condition could exclude from her gross income under section 104(a)(2) a settlement payment received from her former employer. The ambiguity in the law concerning this issue suggests that careful attention and research are required if a client receives damages or settlement payments in a context in which the client might have suffered from emotional distress.

c. Even if a taxpayer suffers only emotional distress, the taxpayer can exclude from gross income an amount of damages received to the extent of medical expenses incurred that were not deducted in prior years. Although the statutory language of section 104(a) is clear that emotional distress is not considered a physical injury, the statutory language also states that this rule does “not apply to an amount of damages not in excess of the amount paid for medical care (described in subparagraph (A) or (B) of section 213(d)(1)) attributable to emotional distress.” For example, in the case discussed above, if the taxpayer had incurred $10,000 in costs for psychological counseling as a result of his emotional distress, then he could have excluded from gross income $10,000 of the $250,000 in settlement payments received from his former employer provided that he had not deducted any portion of the medical expenses in a prior year. If taxpayer had deducted in a prior year $4,000 of the $10,000 in medical expenses incurred, then he could have excluded $6,000 of the $250,000 in settlement payments received from his former employer.

3. Like the Energizer Bunny, the issues surrounding the section 164(b)(6) $10,000 limit on the personal deduction for state and local taxes just keep going . . . and going . . . and going . . . .

The tax benefit rule has long required taxpayers to include in gross income amounts deducted in a prior tax year that are recovered in the current tax year; however, under section 111(a), the amount so includible in gross income is limited to the amount deducted that resulted in a reduction of the taxpayer’s tax liability for the prior year. In other words, the inclusion in gross income of the amount recovered is limited to the “tax benefit” of the amount previously deducted. Likewise, if a taxpayer’s deduction for personal state and local taxes was limited to $10,000 for a prior year (e.g., 2018) by new section 164(b)(6), then a portion of the taxpayer’s personal state and local tax refund received in the current year (e.g., 2019) should be excludable from gross income for the current year under section 111. The question, of course, is determining exactly how much of a taxpayer’s personal state and local tax refund is excludable for the current year under section 111, especially when the $12,000 standard deduction might have been used by the taxpayer had he or she paid the proper amount of personal state and local taxes due for the prior year instead of making an overpayment.

Revenue Ruling 2019-11 holds that the proper amount includible in gross income in these circumstances under section 111 is the lesser of (1) the difference between the taxpayer’s total itemized deductions taken in the prior year and the amount of itemized deductions the taxpayer would have taken in the prior year had the taxpayer paid the proper amount of state and local tax or (2) the difference between the taxpayer’s itemized deductions taken in the prior year and the standard deduction amount for the prior year if the taxpayer was not precluded from taking the standard deduction in the prior year. The above holding applies to the recovery of any state or local tax, including state or local income tax and state or local real or personal property tax.

To assist taxpayers in determining the proper amount excludable from gross income under section 111 with respect to a refund of personal state and local taxes subject to the $10,000 limit of section 164(b)(6) for a prior year, Revenue Ruling 2019-11 provides several helpful examples. In each example, it is assumed that the taxpayers are unmarried individuals whose filing status is “single” and who itemized deductions on their federal income tax returns for 2018 in lieu of using the standard deduction of $12,000. It is further assumed that the taxpayers did not pay or accrue the taxes in carrying on a trade or business or an activity described in section 212. Moreover, it is assumed that for 2018 the taxpayers were not subject to the alternative minimum tax under section 55 and were not entitled to any credit against income tax. Finally, it is assumed that the taxpayers use the cash receipts and disbursements method of accounting.

Situation 1 (State income tax refund fully includable).

Facts: Taxpayer A paid local real property taxes of $4,000 and state income taxes of $5,000 in 2018. A’s state and local tax deduction was not limited by section 164(b)(6) because it was below $10,000. Including other allowable itemized deductions, A claimed a total of $14,000 in itemized deductions on A’s 2018 federal income tax return. In 2019, A received a $1,500 state income tax refund due to A’s overpayment of state income taxes in 2018.

Held: In 2019, A received a $1,500 refund of state income taxes paid in 2018. Had A paid only the proper amount of state income tax in 2018, A’s state and local tax deduction would have been reduced from $9,000 to $7,500 and as a result, A’s itemized deductions would have been reduced from $14,000 to $12,500, a difference of $1,500. A received a tax benefit from the overpayment of $1,500 in state income tax in 2018. Thus, A is required to include the entire $1,500 state income tax refund in A’s gross income in 2019.

Situation 2 (State income tax refund not includable).

Facts: Taxpayer B paid local real property taxes of $5,000 and state income taxes of $7,000 in 2018. Section 164(b)(6) limited B’s state and local tax deduction on B’s 2018 federal income tax return to $10,000, so B could not deduct $2,000 of the $12,000 state and local taxes paid. Including other allowable itemized deductions, B claimed a total of $15,000 in itemized deductions on B’s 2018 federal income tax return. In 2019, B received a $750 state income tax refund due to B’s overpayment of state income taxes in 2018.

Held: In 2019, B received a $750 refund of state income taxes paid in 2018. Had B paid only the proper amount of state income tax in 2018, B’s state and local tax deduction would have remained the same ($10,000) and B’s itemized deductions would have remained the same ($15,000). B received no tax benefit from the overpayment of $750 in state income tax in 2018. Thus, B is not required to include the $750 state income tax refund in B’s gross income in 2019.

Situation 3 (State income tax refund partially includable).

Facts: Taxpayer C paid local real property taxes of $5,000 and state income taxes of $6,000 in 2018. Section 164(b)(6) limited C’s state and local tax deduction on C’s 2018 federal income tax return to $10,000, so C could not deduct $1,000 of the $11,000 state and local taxes paid. Including other allowable itemized deductions, C claimed a total of $15,000 in itemized deductions on C’s 2018 federal income tax return. In 2019, C received a $1,500 state income tax refund due to C’s overpayment of state income taxes in 2018.

Held: In 2019, C received a $1,500 refund of state income taxes paid in 2018. Had C paid only the proper amount of state income tax in 2018, C’s state and local tax deduction would have been reduced from $10,000 to $9,500 and as a result, C’s itemized deductions would have been reduced from $15,000 to $14,500, a difference of $500. C received a tax benefit from $500 of the overpayment of state income tax in 2018. Thus, C is required to include $500 of C’s state income tax refund in C’s gross income in 2019.

Situation 4 (Standard deduction).

Facts: Taxpayer D paid local real property taxes of $4,250 and state income taxes of $6,000 in 2018. Section 164(b)(6) limited D’s state and local tax deduction on D’s 2018 federal income tax return to $10,000, so D could not deduct $250 of the $10,250 state and local taxes paid. Including other allowable itemized deductions, D claimed a total of $12,500 in itemized deductions on D’s 2018 federal income tax return. In 2019, D received a $1,000 state income tax refund due to D’s overpayment of state income taxes in 2018.

Held: In 2019, D received a $1,000 refund of state income taxes paid in 2018. Had D paid only the proper amount of state income tax in 2018, D’s state and local tax deduction would have been reduced from $10,000 to $9,250, and, as a result, D’s itemized deductions would have been reduced from $12,500 to $11,750, which is less than the standard deduction of $12,000 that D would have taken in 2018. The difference between D’s claimed itemized deductions ($12,500) and the standard deduction D could have taken ($12,000) is $500. D received a tax benefit from $500 of the overpayment of state income tax in 2018. Thus, D is required to include $500 of D’s state income tax refund in D’s gross income in 2019.

4. A stockbroker could not assign income to his defunct corporation, says the Tax Court.

In Frey v. Commissioner, the taxpayer, who began working as a stockbroker in 1962, was the chief operating officer of three firms, including Queen City Securities and Jettrade, Inc. During the years in question, 2012 and 2013, the taxpayer was the sole shareholder of Queen City Securities and served as president and chief executive officer of Jettrade, in which he held a majority equity interest. Following a series of financial crises, Queen City ceased to conduct business in 1990. The taxpayer claimed that Queen City had net operating losses or bad debt losses carried forward from years prior to 1991.

During 2012 and 2013, the taxpayer received compensation from Jettrade of $214,150 and $205,300, respectively, and assigned all of the income to Queen City. He prepared his own federal income tax returns for 2012 and 2013 (in part because he had been dissatisfied with and fired professionals with whom he had worked in the past), which included a Schedule C, Profit or Loss from Business, on which he reported that he worked as a stockbroker as a sole proprietor. On Schedule C, the taxpayer included as income the compensation he received from Jettrade and deducted equal amounts as “commissions and fees” for amounts he allegedly paid to Queen City with the intent to utilize Queen City’s loss carryforwards to offset the income. The Service disallowed the deductions on Schedule C for the amounts paid to Queen City and, as a result, made computational adjustments to increase the taxable portion of the Social Security benefits received by the taxpayer and his wife.

The Tax Court (Judge Cohen) agreed with the Service and held that the taxpayer could not assign his income to Queen City. According to the court, it is well established by cases such as Lucas v. Earl that income is taxable to the person who earns it. The proper taxpayer is the person or entity that controls the earning of the income, not the person or entity that ultimately receives it. The court rejected the taxpayer’s rather confused arguments to the contrary, concluded that he had presented no evidence that he had actually transferred funds to Queen City, and also concluded that his testimony at trial was implausible and unreliable and not entitled to any weight.

The court also upheld the Service’s imposition of accuracy-related penalties under section 6662(a), (b)(1) and (b)(2) for both substantial understatement of income tax and negligence. The Service established that there was a substantial understatement of income because the understatement exceeded the greater of ten percent of the tax required to be shown on the return or $5,000. The court held that the evidence established that the taxpayer and his wife were negligent because they “did not consult competent professionals or otherwise attempt to determine their correct tax liabilities.” They did not establish a reasonable cause defense.

5. Only a portion of more than $350,000 of canceled debt was excluded from an individual’s gross income because only a small portion was qualified principal residence indebtedness and the individual was insolvent by approximately $43,000, says the Tax Court.

In Bui v. Commissioner, the taxpayer, Mary Bui ultimately acquired sole ownership of real property in San Jose, California, known as the Red River property, which she used as her principal residence until it was sold in a short sale on March 14, 2011. After the sale of the Red River property, the taxpayer moved into other real property she owned in San Jose, known as the Cedar Grove property, and made it her principal residence. Prior to the date she moved in, the Cedar Grove property had been a rental property. In 2007, the taxpayer had obtained three home-equity lines of credit from Wells Fargo, one of which was secured by the Red River property and two of which were secured by the Cedar Grove property. The taxpayer spent $10,000 in 2007 for custom drapes and $12,000 in 2008 for driveway repair and expansion work at the Red River property and testified to a number of other improvements to the property but provided no documentation of those other expenditures. She provided no evidence of improvements to the Cedar Grove property.

In 2011, Wells Fargo canceled the three home-equity lines of credit and issued Forms 1099-C reporting total canceled indebtedness of $355,488. On her federal income tax return for 2011, the taxpayer excluded all of the canceled debt from gross income as qualified principal residence indebtedness pursuant to section 108(a)(1)(E) (a provision that expired at the end of 2017). The Service took the position that she had to include all of the canceled debt in her gross income.

a. Only $12,000 of the canceled debt was qualified principal residence indebtedness. The Tax Court (Judge Goeke) first concluded that, of the $355,488 of canceled debt, only $12,000 met the definition of “qualified principal residence indebtedness.” That term is defined in section 108(h)(2), which provides that a taxpayer can treat up to $2 million as qualified principal residence indebtedness if the debt is “acquisition indebtedness (within the meaning of section 163(h)(3)(B)) . . . with respect to the principal residence of the taxpayer.” The term “acquisition indebtedness,” as defined in section 163(h)(3)(B), means indebtedness “incurred in acquiring, constructing, or substantially improving any qualified residence of the taxpayer . . . [that] is secured by such [qualified] residence.”

The Tax Court held that the two Wells Fargo lines of credit secured by the Cedar Grove property could not be qualified principal residence indebtedness because the taxpayer had not incurred the debt to acquire or improve that property. (Although not discussed by the court, another reason those lines of credit could not be qualified principal residence indebtedness was that, even if the taxpayer had used the loan proceeds to make improvements to the Cedar Grove property prior to 2011, that property was not her principal residence at that time.)

With respect to the Red River property, the court held that the $10,000 that the taxpayer had spent on custom drapes was not a “substantial improvement” to the property, but that the $12,000 she had spent on driveway expansion and repair was a substantial improvement. The taxpayer had not substantiated any other improvements to the Red River property. The court also concluded that the taxpayer had used the line of credit loan proceeds to pay the $12,000 spent on driveway expansion and repair. Therefore, of the one Wells Fargo line of credit secured by the Red River property, only $12,000 was qualified principal residence indebtedness.

b. Of the $12,000 of qualified principal residence indebtedness, the taxpayer could exclude only $5,299 from her gross income. The Tax Court held that, of the $12,000 that was qualified principal residence indebtedness, the taxpayer could exclude from her gross income only $5,299 because of the limitation in section 108(h)(4). Section 108(h)(4) provides that, if only a portion of canceled debt is qualified principal residence indebtedness, then a taxpayer can exclude from gross income only “so much of the amount discharged as exceeds the amount of the loan (as determined immediately before such discharge) which is not qualified principal residence indebtedness.” In this case, the total amount of the loan secured by the Red River property was $250,000, of which $243,299 was canceled. Of the total $250,000 loan amount, $238,000 ($250,000-$12,000) was not qualified principal residence indebtedness. Therefore, under section 108(h)(4), the limit on the amount the taxpayer could exclude from gross income was $5,299 ($243,299 canceled debt-$238,000).

The effect of the section 108(h)(4) limitation is to treat the taxpayer as having paid a portion of the loan that was qualified principal residence indebtedness and to treat Wells Fargo as having canceled the portion of the loan that was not qualified principal residence indebtedness. Of the $250,000 loan amount, Wells Fargo canceled $243,299, which means that $6,701 of the loan was paid from the proceeds of the short sale of the Red River property. In effect, section 108(h)(4) treats this payment of $6,701 as having been made on the $12,000 portion of the loan that was qualified principal residence indebtedness, leaving only $5,299 ($12,000-$6,701) of qualified principal residence indebtedness that was canceled.

c. The taxpayer was insolvent by $42,852 and therefore could exclude this amount of canceled debt from her gross income. Under section 108(a)(1)(B), a taxpayer can exclude canceled debt from gross income if the taxpayer is insolvent, and section 108(a)(3) limits the exclusion to the amount by which the taxpayer is insolvent. For this purpose, the term “insolvent” is defined in section 108(d)(3), which provides that a taxpayer is insolvent to the extent that, immediately before the cancellation of indebtedness, the taxpayer’s liabilities exceed the fair market value of the taxpayer’s assets. As part of their preparation for trial in the Tax Court, the taxpayer and the Service had stipulated that the taxpayer was insolvent to the extent of $42,852. Accordingly, the Tax Court held that the taxpayer could exclude this amount of the canceled debt from gross income (in addition to the $5,299 she could exclude from gross income as a cancellation of qualified principal residence indebtedness).

6. Congress has extended through 2020 the exclusion for discharge of qualified principal residence indebtedness.

Section 101 of the Taxpayer Certainty and Disaster Tax Relief Act of 2019 retroactively extended through December 31, 2020, the section 108(a)(1)(E) exclusion for up to $2 million ($1 million for married individuals filing separately) of income from the cancellation of qualified principal residence indebtedness. Thus, the exclusion applies for calendar years 2018, 2019, and 2020. Amendment of 2018 returns might be necessary.

7. Volunteer firefighters and emergency medical responders can exclude from gross income any reduction or rebate of state or local tax and up to $50 per month of any payments they receive for their service, but only for 2020.

Section 301 of the Setting Every Community Up for Retirement Enhancement Act of 2019 (SECURE Act) reinstated section 139B. Section 139B allows volunteer firefighters and emergency medical responders to exclude from gross income any reduction or rebate of state or local tax they receive for their service as well as up to $50 per month of any payment they receive on account of their service. Congress enacted section 139B in 2007 but the provision had expired for taxable years beginning after 2010. As amended, section 139B now applies only to taxable years beginning after December 31, 2019, and before January 1, 2021, i.e., it applies only for 2020.

C. Hobby Losses and Section 280A Home Office and Vacation Homes

There were no significant developments regarding this topic during 2019.

D. Deductions and Credits for Personal Expenses

1. Has the federal deduction for your high property or state income taxes made them easier to bear? Brace yourself! The deduction for state and local taxes not paid or accrued in carrying on a trade or business or an income-producing activity is limited to $10,000.

Section 11042 of the TCJA amended section 164(b) by adding section 164(b)(6). For individual taxpayers, this provision generally (1) eliminates the deduction for foreign real property taxes and (2) limits to $10,000 ($5,000 for married individuals filing separately) a taxpayer’s itemized deductions on Schedule A for the aggregate of state or local property taxes, income taxes, and sales taxes deducted in lieu of income taxes. This provision applies to taxable years beginning after 2017 and before 2026. The provision does not affect the deduction of state or local property taxes or sales taxes that are paid or accrued in carrying on a trade or business or an income-producing activity (i.e., an activity described in section 212) that are properly deductible on Schedules C, E, or F. For example, property taxes imposed on residential rental property will continue to be deductible. With respect to income taxes, an individual can deduct only foreign income taxes paid or accrued in carrying on a trade or business or an income-producing activity. As under current law, an individual cannot deduct state or local income taxes as a business expense even if the individual is engaged in a trade or business as a sole proprietor.

a. The Service is not going to give blue states a pass on creative workarounds to the new $10,000 limitation on the personal deduction for state and local taxes. In response to new section 164(b)(6), many states—including Connecticut, New Jersey, and New York—enacted workarounds to the $10,000 limitation. For instance, New Jersey reportedly enacted legislation giving property owners a special tax credit against otherwise assessable property taxes if the owner makes a contribution to charitable funds designated by local governments. Connecticut reportedly enacted a new provision that taxes the income of pass-through entities such as S corporations and partnerships, but allows the shareholders or members a corresponding tax credit against certain state and local taxes assessed against them individually. In Notice 2018-54, the Service announced that it was aware of these workarounds and that proposed regulations would be issued to “make clear that the requirements of the Internal Revenue Code, informed by substance-over-form principles, govern the federal income tax treatment of such transfers.” In other words, blue states, don’t bank on a charitable contribution or a flow-through income tax substituting for otherwise assessable state and local taxes to avoid new section 164(b)(6). The authors predict that this will be an interesting subject to watch over the coming months.

b. Speaking of looming trouble spots: The availability of a business expense deduction under section 162 for payments to charities is not affected by the recently issued Proposed Regulations, says the Service. In a news release, the Service clarified that the availability of a deduction for ordinary and necessary business expenses under section 162 for businesses that make payments to charities or government agencies, and for which the business receives state tax credits, is not affected by the Proposed Regulations issued in August 2018, which generally disallow a federal charitable contribution deduction under section 170 for charitable contributions made by an individual for which the individual receives a state tax credit. Thus, if a payment to a government agency or charity qualifies as an ordinary and necessary business expense under section 162(a), it is not subject to disallowance in the manner in which deductions under section 170 are subject to disallowance. This is true, according to the news release, regardless of whether the taxpayer is doing business as a sole proprietor, partnership, or corporation. According to a “frequently asked question” posted on the Service’s website, “a business taxpayer making a payment to a charitable or government entity described in § 170(c) is generally permitted to deduct the entire payment as an ordinary and necessary business expense under § 162 if the payment is made with a business purpose.”

c. More about trouble spots: The Service must be thinking “will this ever end?” Notwithstanding the above guidance, the Treasury Department and the Service obviously have continued to receive questions regarding the deductibility of business expenses that may indirectly bear on the taxpayer’s state and local tax liability. In response, Revenue Procedure 2019-12 provides certain safe harbors. For C corporations that make payments to or for the use of section 170(c) charitable organizations and that receive or expect to receive corresponding tax credits against state or local taxes, the C corporation nevertheless may treat such payments as meeting the requirements of an ordinary and necessary business expense for purposes of section 162(a).

A similar safe-harbor rule applies for entities other than C corporations, but only if the entity is a “specified passthrough entity.” A specified passthrough entity for this purpose is one that meets four requirements. First, the entity must be a business entity other than a C corporation that is regarded for all federal income tax purposes as separate from its owners under Regulation section 301.7701-3 (i.e., it is not single-member LLC). Second, the entity must operate a trade or business within the meaning of section 162. Third, the entity must be subject to a state or local tax incurred in carrying on its trade or business that is imposed directly on the entity. Fourth, in return for a payment to a section 170(c) charitable organization, the entity receives or expects to receive a state or local tax credit that the entity applies or expects to apply to offset a state or local tax imposed upon the entity. The Revenue Procedure applies to payments made on or after January 1, 2018.

Revenue Procedure 2019-12 provides the following examples of the safe-harbor rules applicable to C corporations and specified passthrough entities:

(i) C corporation example state and local income tax credit: A, a C corporation engaged in a trade or business, makes a payment of $1,000 to a section 170(c) charitable organization. In return for the payment, A receives or expects to receive a dollar-for-dollar state tax credit to be applied to A’s state corporate income tax liability. Under the Revenue Procedure, A may treat the $1,000 payment as meeting the requirements of an ordinary and necessary business expense under section 162.

(ii) C corporation example state and local property tax credit: B, a C corporation engaged in a trade or business, makes a payment of $1,000 to a section 170(c) charitable organization. In return for the payment, B receives or expects to receive a tax credit equal to 80% of the amount of this payment ($800) to be applied to B’s local real property tax liability. Under the Revenue Procedure, B may treat $800 as meeting the requirements of an ordinary and necessary business expense under section 162. The treatment of the remaining $200 will depend upon the facts and circumstances and is not affected by the Revenue Procedure.

(iii) Specified passthrough example state and local property tax credit: S is an S corporation engaged in a trade or business and is owned by individuals C and D. S makes a payment of $1,000 to a section 170(c) charitable organization. In return for the payment, S receives or expects to receive a state tax credit equal to 80% of the amount of this payment ($800) to be applied to S’s local real property tax liability incurred by S in carrying on its trade or business. Under applicable state and local law, the real property tax is imposed at the entity level (not the owner level). Under the Revenue Procedure, S may treat $800 of the payment as meeting the requirements of an ordinary and necessary business expense under section 162. The treatment of the remaining $200 will depend upon the facts and circumstances and is not affected by this Revenue Procedure.

d. And like Rameses II in The Ten Commandments, the Treasury says, “so let it be written; so let it (finally!) be done.” The Treasury Department and the Service have finalized, with only minor changes, proposed amendments to the Regulations under section 170 that purport to close the door on any state-enacted workarounds to the $10,000 limitation of section 164(b)(6) on a taxpayer’s itemized deductions. Regulation section 1.170A-1(h)(3) generally requires taxpayers to reduce the amount of any federal income tax charitable contribution deduction by the amount of any corresponding state or local tax credit the taxpayer receives or expects to receive. The final Regulations further provide that a corresponding state or local tax deduction normally will not reduce the taxpayer’s federal deduction provided the state and local deduction does not exceed the taxpayer’s federal deduction. To the extent the state and local charitable deduction exceeds the taxpayer’s federal deduction, the taxpayer’s federal deduction is reduced. Finally, the final Regulations provide an exception whereby the taxpayer’s federal charitable contribution deduction is not reduced if the corresponding state or local credit does not exceed 15% of the taxpayer’s federal deduction. Pursuant to an amendment to Regulation section 1.642(c)-3(g), these same rules apply in determining the charitable contribution deductions of trusts and estates under section 642(c).

Three examples in the Regulations illustrate the application of these rules:

Example 1. A, an individual, makes a payment of $1,000 to X, an entity listed in section 170(c). In exchange for the payment, A receives or expects to receive a state tax credit of 70% of the amount of A’s payment to X. Under paragraph (h)(3)(i) of this section, A’s charitable contribution deduction is reduced by $700 (0.70 × $1,000). This reduction occurs regardless of whether A may claim the state tax credit in that year. Thus, A’s charitable contribution deduction for the $1,000 payment to X may not exceed $300.
Example 2. B, an individual, transfers a painting to Y, an entity listed in section 170(c). At the time of the transfer, the painting has a fair market value of $100,000. In exchange for the painting, B receives or expects to receive a state tax credit equal to 10 percent of the fair market value of the painting. Under paragraph (h)(3)(vi) of this section, B is not required to apply the general rule of paragraph (h)(3)(i) of this section because the amount of the tax credit received or expected to be received by B does not exceed 15 percent of the fair market value of the property transferred to Y. Accordingly, the amount of B’s charitable contribution deduction for the transfer of the painting is not reduced under paragraph (h)(3)(i) of this section.
Example 3. C, an individual, makes a payment of $1,000 to Z, an entity listed in section 170(c). In exchange for the payment, under state M law, C is entitled to receive a state tax deduction equal to the amount paid by C to Z. Under paragraph (h)(3)(ii)(A) of this section, C is not required to reduce its charitable contribution deduction under section 170(a) on account of the state tax deduction.

(i) Effective date. The final Regulations are effective for charitable contributions made after August 27, 2018.

(ii) And another thing . . . . The final Regulations do not discern between abusive “workarounds” enacted in response to section 164(b)(6) and legitimate state and local tax credit programs such as the Georgia Rural Hospital Tax Credit that preceded the TCJA. The Georgia Rural Hospital Tax Credit program was enacted in 2017 to combat the closure of many rural hospitals in Georgia due to financial difficulties. Under the program, individuals and corporations making contributions to designated rural hospitals receive a 90% dollar-for-dollar tax credit against their Georgia state income tax liability. Is the Georgia Rural Hospital Tax Credit program adversely affected by the Regulations under section 164(b)(6)? In our view, the answer is “yes,” and a Georgia taxpayer’s federal charitable contribution deduction for a donation to a Georgia rural hospital is reduced by 90%. The Treasury Department and the Service have adopted this view, which is reflected in the Preamble to the final Regulations:

The regulations are based on longstanding federal tax law principles that apply equally to all taxpayers. To ensure fair and consistent treatment, the final regulations do not distinguish between taxpayers who make transfers to state and local tax credit programs enacted after the [TCJA] and those who make transfers to tax credit programs existing prior to the enactment of the Act. Neither the intent of the section 170(c) organization, nor the date of enactment of a particular state tax credit program, are relevant to the application of the quid pro quo principle.

We note, however, that it may be possible under state or local law for a taxpayer to waive any corresponding state or local tax credit and thereby claim a full charitable contribution for federal income tax purposes. In the Preamble to the final Regulations, the Treasury Department and the Service noted that taxpayers might disclaim a credit by not applying for it if the credit calls for an application (or applying for a lesser amount) and requested comments as to how taxpayers may decline state or local tax credits in other situations. It is also possible, pursuant to a safe harbor established in Notice 2019-12 (see below), for an individual who itemizes deductions to treat as a payment of state or local tax on Schedule A payments made to a charitable organization for which the individual receives a state or local tax credit.

e. Down the rabbit hole we go. A safe harbor allows individuals who itemize to treat as payments of state or local tax any payments to section 170(c) charitable organizations that are disallowed as federal charitable contribution deductions because the individual will receive a state or local tax credit for the payment. In Notice 2019-12, the Treasury Department and the Service announced they intend to publish proposed regulations that will amend Regulation section 1.164-3 to provide a safe harbor for individuals who itemize deductions and make a payment to or for the use of an entity described in section 170(c) in return for a state or local tax credit. Until the proposed regulations are issued, taxpayers can rely on the safe harbor as set forth in the Notice. Section 3 of the Notice provides as follows:

Under this safe harbor, an individual who itemizes deductions and who makes a payment to a section 170(c) entity in return for a state or local tax credit may treat as a payment of state or local tax for purposes of section 164 the portion of such payment for which a charitable contribution deduction under section 170 is or will be disallowed under final regulations. This treatment as a payment of state or local tax under section 164 is allowed in the taxable year in which the payment is made to the extent the resulting credit is applied, consistent with applicable state or local law, to offset the individual’s state or local tax liability for such taxable year or the preceding taxable year. To the extent the resulting credit is not applied to offset the individual’s state or local tax liability for the taxable year of the payment or the preceding taxable year, any excess credit permitted to be carried forward may be treated as a payment of state or local tax under section 164 in the taxable year or years for which the carryover credit is applied, consistent with applicable state or local law, to offset the individual’s state or local tax liability.

The safe harbor does not apply to a transfer of property and does not permit a taxpayer to treat the amount of any payment as deductible under more than one provision of the Code or regulations. The safe harbor applies to payments made after August 27, 2018. Three examples illustrate the application of these rules:

Example 1. In year 1, Taxpayer A makes a payment of $500 to an entity described in section 170(c). In return for the payment, A receives a dollar-for-dollar state income tax credit. Prior to application of the credit, A’s state income tax liability for year 1 was $500 or more; A applies the $500 credit to A’s year 1 state income tax liability. Under section 3 of this notice, A treats the $500 payment as a payment of state income tax in year 1 for purposes of section 164. To determine A’s deduction amount, A must apply the provisions of section 164 applicable to payments of state and local taxes, including the limitation under section 164(b)(6).
Example 2. In year 1, Taxpayer B makes a payment of $7,000 to an entity described in section 170(c). In return for the payment, B receives a dollar-for-dollar state income tax credit, which under state law may be carried forward for three taxable years. Prior to application of the credit, B’s state income tax liability for year 1 was $5,000; B applies $5,000 of the $7,000 credit to B’s year 1 state income tax liability. Under section 3 of this notice, B treats $5,000 of the $7,000 payment as a payment of state income tax in year 1 for purposes of section 164. Prior to application of the remaining credit, B’s state income tax liability for year 2 exceeds $2,000; B applies the excess credit of $2,000 to B’s year 2 state income tax liability. For year 2, B treats the $2,000 as a payment of state income tax for purposes of section 164. To determine B’s deduction amounts in years 1 and 2, B must apply the provisions of section 164 applicable to payments of state and local taxes, including the limitation under section 164(b)(6).
Example 3. In year 1, Taxpayer C makes a payment of $7,000 to an entity described in section 170(c). In return for the payment, C receives a local real property tax credit equal to 25 percent of the amount of this payment ($1,750). Prior to application of the credit, C’s local real property tax liability in year 1 was $3,500; C applies the $1,750 credit to C’s year 1 local real property tax liability. Under section 3 of this notice, for year 1, C treats $1,750 as a payment of local real property tax for purposes of section 164. To determine C’s deduction amount, C must apply the provisions of section 164 applicable to payments of state and local taxes, including the limitation under section 164(b)(6).

f. Proposed Regulations reflect previously issued guidance on payments to section 170(c) charitable organizations that result in state or local tax credits and provide additional guidance. The Treasury Department and the Service have issued Proposed Regulations that reflect previously issued guidance, including safe harbors, regarding payments to section 170(c) charitable organizations that result in state or local tax credits. The Proposed Regulations generally provide the following guidance.

(i) Safe harbors for payments by C corporations and specified pass-through entities to section 170(c) entities. The Proposed Regulations propose amending Regulation section 1.162-15(a) to incorporate the safe harbors previously set forth in Revenue Procedure 2019-12. One safe harbor provides that C corporations that make payments to or for the use of section 170(c) charitable organizations and that receive or expect to receive corresponding tax credits against state or local taxes may treat such payments as meeting the requirements of an ordinary and necessary business expense for purposes of section 162(a).

A similar safe-harbor rule applies for entities other than C corporations but only if the entity is a “specified passthrough entity.” A specified passthrough entity for this purpose is one that meets four requirements. First, the entity must be a business entity other than a C corporation that is regarded for all federal income tax purposes as separate from its owners under Regulation section 301.7701-3 (i.e., it is not single-member LLC). Second, the entity must operate a trade or business within the meaning of section 162. Third, the entity must be subject to a state or local tax incurred in carrying on its trade or business that is imposed directly on the entity. Fourth, in return for a payment to a section 170(c) charitable organization, the entity receives or expects to receive a state or local tax credit that the entity applies or expects to apply to offset a state or local tax imposed upon the entity. These safe harbors apply only to payments of cash and cash equivalents.

The amendments are proposed to apply to payments on or after December 17, 2019, but taxpayers may continue to apply Revenue Procedure 2019-12, which applies to payments made on or after January 1, 2018.

(ii) Amendments to clarify the standard for payments to a charitable organization to qualify as a business expense. The Proposed Regulations also propose amending Regulation section 1.162-15(a) to provide:

A payment or transfer to or for the use of an entity described in section 170(c) that bears a direct relationship to the taxpayer’s trade or business and that is made with a reasonable expectation of financial return commensurate with the amount of the payment or transfer may constitute an allowable deduction as a trade or business expense rather than a charitable contribution deduction under section 170.

This proposed revision is intended to more clearly reflect current law regarding when payments from a business to a charitable organization qualify as a business expense (rather than as a charitable contribution). The Proposed Regulations provide two examples, both of which involve businesses making payments to a section 170(c) charitable organization in exchange for advertising (e.g., a half-page advertisement in the program for a church concert) or to generate name recognition and goodwill (e.g., donating one percent of gross sales to a charity each year).

These amendments are proposed to apply to payments or transfers on or after December 17, 2019, but taxpayers may rely on the Proposed Regulations for payments and transfers made on or after January 1, 2018, and before the date final regulations are published in the Federal Register.

(iii) A safe harbor for individuals who itemize deductions. The Proposed Regulations propose amending Regulation section 1.164-3(j) to incorporate the safe harbor previously provided in Notice 2019-12. Under this safe harbor, an individual who itemizes deductions and who makes a payment to a section 170(c) entity in return for a state or local tax credit may treat as a payment of state or local tax for purposes of section 164 the portion of the payment for which a charitable contribution deduction under section 170 is disallowed by Regulation section 1.170A-1(h)(3). This latter Regulation generally disallows a taxpayer’s federal charitable contribution deduction to the extent the taxpayer receives a state or local tax credit in exchange for a payment to a section 170(c) entity. For example, the proposed safe harbor would permit an individual who makes a $1,000 payment to a section 170(c) entity and who, in exchange, receives a $700 state or local tax credit to treat the $700 that is disallowed as a federal charitable contribution deduction as a payment of state or local tax that is deductible on Schedule A, subject to the $10,000 limit of section 164(b)(6).

These amendments are proposed to apply to payments made on or after June 11, 2019 (the date the Service issued Notice 2019-12), but individuals can rely on the Proposed Regulations for payments made after August 27, 2018, and before the date final regulations are published in the Federal Register.

(iv) Amendments to clarify the effect of benefits provided to a donor that are not provided by the section 170(c) entity. The Proposed Regulations propose amending Regulation section 1.170A-1(h)(4)(i) to provide:

A taxpayer receives goods or services in consideration for a taxpayer’s payment or transfer to an entity described in section 170(c) if, at the time the taxpayer makes the payment to such entity, the taxpayer receives or expects to receive goods or services from that entity or any other party in return.

This amendment is intended to clarify that the quid pro quo principle, under which a taxpayer’s charitable contribution deduction is disallowed to the extent the taxpayer receives goods or services in return, applies regardless of whether the goods or services are provided by the section 170(c) entity receiving the contribution. The Preamble to the Proposed Regulations discusses judicial decisions that have adopted this approach, such as Singer v. United States and Wendell Falls Development, LLC v. Commissioner. The Service reached a similar result in example 11 of Revenue Ruling 67-246, in which a taxpayer who made a $100 payment to a specific charity and, in return, received a transistor radio worth $15 from a local store could take a charitable contribution deduction of only $85. The Proposed Regulations also propose to amend Regulation section 1.170A-1(h)(4)(ii) to define “goods or services” for this purpose as “cash, property, services, benefits, and privileges.”

These amendments are proposed to apply to amounts paid or property transferred after December 17, 2019. Nevertheless, because the amendments are intended to reflect current law, they effectively apply immediately.

2. The Tax Court reiterates that it does not have equitable power to change the statutory treatment of excess advance premium tax credits as an increase in tax.

In Kerns v. Commissioner, the taxpayers, a married couple, purchased health insurance for 2014 through Covered California, a health insurance exchange created under the Affordable Care Act. Based on their projected household income, they qualified for an advance payment of the premium tax credit authorized by section 36B. During 2014, the exchange made total payments to the health insurance issuer of $8,402.

Generally, under section 36B(c)(1), the premium tax credit is available to taxpayers whose household income is at least 100% but not more than 400% of the federal poverty line. For this purpose, section 36B(d)(2)(A) provides that household income is the sum of the modified adjusted gross income (MAGI) of the taxpayer and all family members required to file a tax return who are taken into account in determining family size. MAGI is defined in relevant part by section 36B(d)(2)(B) as AGI increased by certain items.

The AGI and MAGI for 2014 of the taxpayers, who had no dependents, was $97,061. This amount exceeded 400% of the federal poverty line, and therefore the taxpayers were not eligible for the section 36B premium tax credit. Because they had received advance credit payments, they were required by section 36B(f)(1) to reconcile the amount of the advance payments with the premium tax credit calculated on their return. The taxpayers did not report their advance credit payments on their 2014 return. The Service ultimately issued a notice of deficiency disallowing the entire credit. Because they did not qualify for any premium tax credit and had received $8,402 in advance credit payments, they owed the entire $8,402 as a tax liability.

The taxpayers asserted various state law claims against the health insurance issuer (Blue Shield) and Covered California, including false advertising, unfair business practices, and breach of duty. They argued that this alleged malfeasance nullified any tax liability arising from the excess advance premium tax credit payments.

The Tax Court (Judge Lauber) held that it had no ability to grant relief to the taxpayers. The court relied on its prior decision in McGuire v. Commissioner for the proposition that the statutory mandate of section 36B(f)(2)(A), which provides that tax liability “shall be increased” by the amount of any excess advance premium tax credit payments, is not subject to equitable exceptions.

3. Although the Tax Court found it more likely than not that the taxpayer’s compulsive gambling was a side effect of his physician-prescribed Pramipexole, his gambling losses were not casualty losses.

In Mancini v. Commissioner, the taxpayer earned good money and was a successful real estate investor who gambled occasionally, but never more than $100 at a time. When he was diagnosed with Parkinson’s disease, his neurologist prescribed Pramipexole (the generic name for Mirapex). Although his symptoms improved, the taxpayer started doing “odd things.” He vacuumed a lot and became compulsive about his cleanliness. He spent a week researching and obsessing over which mattress to buy. He started falling asleep suddenly while driving. He had suicidal thoughts. And he started gambling—a lot.

Over the next two years the taxpayer depleted his bank accounts and all but $10,000 of his retirement savings. He also sold his real estate for less than fair market value and used the proceeds to pay gambling debts. On the taxpayer’s 2008 and 2009 returns, for which he retained a return preparer, he reported gambling winnings and deducted gambling losses up to the amount of his gambling winnings. He prepared his 2010 return himself and deducted gambling losses up to the amount of his gambling winnings, and also deducted a $603,000 casualty loss for “Investment Portfolio and Home.” He later amended his 2008 and 2009 returns to claim large casualty losses. The Service issued a notice of deficiency for 2010.

The Tax Court (Judge Holmes) first concluded, based on expert testimony, that it was more likely than not that the taxpayer’s compulsive gambling was a side effect of the Pramipexole he was taking. Nevertheless, the court held that the taxpayer’s gambling losses were not casualty losses for two reasons. First, the court reasoned, physical damage to property is a prerequisite of a casualty-loss deduction, and the taxpayer had not suffered physical damage to property. Mancini’s depleted bank accounts, and the money he left on the table when he made bad real estate deals, did not result in any physical damage. Second, the manner in which casualty losses are calculated demonstrates that the taxpayer had not suffered a casualty loss. The amount of a casualty loss is the amount by which the fair market value of the property before the casualty exceeds the fair market value of the property after the casualty, reduced by the amount of any insurance proceeds recovered. In this case, the court reasoned, the taxpayer’s losses occurred over three years, which is not “sudden” as required for a casualty loss, and it would be difficult or impossible to apply a before-and-after test to determine the amount of his loss because his “losses were necessarily the result of dozens or hundreds of individual gambling sessions and probably thousands of separate wagers.” The court also held that, even if the losses were casualty losses, the taxpayer had failed to substantiate them.

Finally, the court declined to impose accuracy-related penalties under by section 6662(a) because the Service had not introduced any evidence that the penalties had been “personally approved (in writing) by the immediate supervisor of the individual making [the initial] determination” of the penalty as required by section 6751(b)(1).

4. In determining eligibility for the section 36B premium tax credit, a taxpayer’s modified adjusted gross income includes lump-sum Social Security benefits attributable to a prior year, even if the taxpayer has made an election under section 86(e).

Section 86(e) permits a taxpayer who receives a lump-sum Social Security payment that is attributable to a prior year to limit the portion that is taxed by electing to include in gross income only the portion of the payment equal to the increase in gross income that would have occurred had the taxpayer taken the payment into account in the prior year to which the payment is attributable. For example, assume that (1) a taxpayer receives a $100 lump-sum Social Security payment this year that is attributable to last year, (2) $60 of the payment would be included in gross income this year, and (3) if the taxpayer had taken the payment into account last year, only $40 would have been included in gross income. The taxpayer in this example could elect under section 86(e) to include in gross income this year only $40 of the payment.

In Johnson v. Commissioner, the issue was the effect of a section 86(e) election on the calculation of a taxpayer’s modified adjusted gross income (MAGI) for purposes of determining eligibility for the premium tax credit authorized by section 36B for individuals who meet certain eligibility requirements and purchase health insurance coverage under a qualified health plan through an Affordable Insurance Exchange. Generally, under section 36B(c)(1), the premium tax credit is available to taxpayers whose household income is at least 100% but not more than 400% of the federal poverty line. For this purpose, section 36B(d)(2)(A) provides that household income is the sum of the MAGI of the taxpayer and all family members required to file a tax return who are taken into account in determining family size. MAGI is defined in relevant part by section 36B(d)(2)(B) as adjusted gross income increased by certain items, including “an amount equal to the portion of the taxpayer’s social security benefits (as defined in section 86(d)) which is not included in gross income under section 86 for the taxable year.”

The taxpayer in this case received total Social Security benefits in 2014 of $26,180, of which $11,092 was attributable to a lump-sum payment relating to 2013. By making a section 86(e) election, the taxpayer limited the taxable portion of the total benefits received in 2014 to $6,687. The taxpayer argued that his MAGI for 2014 as defined in section 36B(d)(2)(B) should include none of the $11,092 of Social Security benefits attributable to 2013 or, at most, should include only the portion of his 2013 benefits included in his gross income for 2014. The taxpayer focused on the statutory phrase “under section 86 for the taxable year” in section 36B(d)(2)(B) and argued that the statute required inclusion in MAGI for 2014 only benefits attributable to the taxable year (2014) for which the determination was being made, and not those attributable to 2013.

The Tax Court (Judge Gerber) held that the taxpayer’s section 86(e) election had no effect on the determination of the taxpayer’s MAGI for 2014. According to the court:

[W]e hold that the text of the statute is not ambiguous and that petitioner must include in his MAGI all of the Social Security benefits received in 2014, irrespective of the section 86(e) election. As a result, petitioner’s adjusted gross income is increased by the amount of Social Security benefits not included in gross income and, as explained below, his MAGI exceeds the established threshold for PTC eligibility by a relatively small amount.

5. Although the Service treats Medicaid waiver payments as excludable from gross income, such payments are earned income for purposes of the earned income credit and the child tax credit, says the Tax Court.

Medicaid waiver payments are payments to individual care providers for the care of eligible individuals under a state Medicaid Home and Community-Based Services waiver program described in section 1915(c) of the Social Security Act. Generally, these payments are made by a state that has obtained a Medicaid waiver that allows the state to include in the state’s Medicaid program the cost of home or community-based services (other than room and board) provided to individuals who otherwise would require care in a hospital, nursing facility, or intermediate care facility. In Notice 2014-7, the Service concluded that Medicaid waiver payments qualify as “difficulty of care payments” within the meaning of section 131(c) and therefore can be excluded from the recipient’s gross income under section 131(a), which excludes amounts received by a foster care provider as qualified foster care payments. Generally, difficulty of care payments are compensation for providing additional care to a qualified foster individual that is required by reason of the individual’s physical, mental, or emotional handicap and that is provided in the home of the foster care provider.

In Feigh v. Commissioner, the taxpayers, a married couple, received Medicaid waiver payments in 2015 in the amount of $7,353, which were reflected on Form W-2, for the care of their disabled adult children. The taxpayers reported this amount as wages on their 2015 return but excluded the payments from gross income. They received no other income during 2015 that would qualify as earned income. The taxpayers claimed an earned income credit of $3,319 and an additional child tax credit of $653. The Service asserted that the Medicaid waiver payment was not earned income and therefore disallowed the taxpayers’ earned income credit and child tax credit.

The Tax Court (Judge Goeke) held that the Medicaid waiver payments in the amount of $7,353 did qualify as earned income for purposes of both the earned income credit and the additional child tax credit. For this purpose, section 32(c)(2)(A)(i) defines “earned income” as “wages, salaries, tips, and other employee compensation, but only if such amounts are includible in gross income for the taxable year.” The court reasoned that, even though the taxpayers did not include in gross income the Medicaid waiver payments they received, the payments were includible in gross income. The court engaged in a lengthy analysis of Notice 2014-7, in which the Service had concluded that such payments could be excluded from gross income under section 131(a), and determined that the notice was entitled to so-called Skidmore deference, under which a government agency’s interpretation is accorded respect befitting “the thoroughness evident in its consideration, the validity of its reasoning, its consistency with earlier and later pronouncements, and all those factors which give it power to persuade, if lacking power to control.” The Tax Court concluded that Notice 2014-7 was “entitled little, if any, deference.” In other words, the court concluded that the Service got it wrong when it determined that the taxpayers’ Medicaid waiver payments were excludable from gross income.

Based on its analysis, the court accepted the taxpayers’ argument that the Service could not reach a result contrary to the Code by reclassifying the taxpayers’ earned income as unearned for purposes of determining eligibility for the tax credits in question. The Service argued that no statutory provision demonstrated that Congress intended to allow a double benefit, that is, both an exclusion of the Medicaid waiver payment from gross income and eligibility for the earned income credit and child tax credit. The court responded: “Respondent’s argument, however, misses that he, not Congress, has provided petitioners with a double tax benefit.”

6. Standard deduction for 2020.

The standard deduction for 2020 will be $24,800 for joint returns and surviving spouses (increased from $24,400), $12,400 for unmarried individuals and married individuals filing separately (increased from $12,200), and $18,650 for heads of households (increased from $18,350). For individuals who can be claimed as dependents, the standard deduction cannot exceed the greater of $1,100 or the sum of $350 and the individual’s earned income. The additional standard deduction amount for those who are legally blind or who are age 65 or older is $1,650 for those with the filing status of single or head of household (and who are not surviving spouses) and is $1,300 for married taxpayers ($2,600 on a joint return if both spouses are age 65 or older).

7. Extension of the 7.5% threshold for deduction of medical expenses through 2020.

Prior to the TCJA, medical expenses generally were deductible only to the extent they exceeded ten percent of a taxpayer’s adjusted gross income. For taxable years beginning after 2012 and ending before 2017, this threshold was reduced to 7.5% if the taxpayer or the taxpayer’s spouse had attained age 65 by the close of the year. Section 11027 of the TCJA amended section 213(f) to provide that the 7.5% threshold applies to all taxpayers for taxable years beginning after 2016 and ending before 2019 (i.e., to calendar years 2017 and 2018). Further, the legislation provided that this threshold applies for purposed of both the regular tax and the alternative minimum tax. Section 103 of the Taxpayer Certainty and Disaster Tax Relief Act of 2019 retroactively extended this reduced threshold to taxable years beginning before January 1, 2021 (i.e., to calendar years 2019 and 2020).

8. Mortgage insurance premiums paid through 2020 remain deductible.

Section 102 of the Taxpayer Certainty and Disaster Tax Relief Act of 2019 retroactively extended through December 31, 2020, the section 163(h)(3)(E) deduction (subject to the pre-existing limitations) for mortgage insurance premiums paid or accrued in connection with acquisition indebtedness with respect to a qualified residence of the taxpayer. Thus, these premiums are deductible for calendar years 2018, 2019, and 2020. Because of its retroactive effect, the amendment of section 163(h)(3)(E) may require the amendment of 2018 returns.

9. A retroactive deduction for paying your child’s college tuition.

Section 104 of the Taxpayer Certainty and Disaster Tax Relief Act of 2019 retroactively extended through December 31, 2020, the section 222 above-the-line deduction for individuals of a limited amount ($0, $2,000, or $4,000, depending on the taxpayer’s adjusted gross income) of qualified tuition and related expenses for higher education of the taxpayer, the taxpayer’s spouse, or dependents. Thus, this deduction is available for calendar years 2018, 2019, and 2020. Because of its retroactive effect, the amendment of section 222 may require the amendment of 2018 returns.

10. Deducting casualty losses arising in qualified disaster areas just got easier.

Section 204(b) of the Taxpayer Certainty and Disaster Tax Relief Act of 2019 provides special rules for disaster losses in qualified disaster areas. Normally, a personal casualty loss is deductible only to the extent that it exceeds $100 and only to the extent the sum of all personal casualty losses exceeds ten percent of adjusted gross income. The legislation provides that a “net disaster loss” is deductible only to the extent it exceeds $500 (rather than $100) and is deductible without regard to the normal ten-percent-of-AGI threshold. An individual with a net disaster loss can deduct the sum of any nondisaster personal casualty losses, which remain subject to the $100 and ten-percent thresholds, and the net disaster loss. For example, if an individual has AGI of $90,000, a nondisaster-related casualty loss of $10,000 from the theft of a personal car, and a net disaster loss of $50,000, then the individual can deduct $900 of the theft loss ($10,000 reduced by $100 reduced by ten percent of AGI) and can deduct $49,500 of the net disaster loss ($50,000 reduced by $500). The deduction for the net disaster loss is available both to those who itemize their deductions and those who do not. For those who do not itemize, the standard deduction is increased by the amount of the net disaster loss. The disallowance of the standard deduction for purposes of determining alternative minimum taxable income does not apply to this increased portion of the standard deduction.

A net disaster loss is defined as the amount by which “qualified disaster-related personal casualty losses” exceed personal casualty gains. A qualified disaster-related personal casualty loss is a loss described in section 165(c)(3) (which generally defines casualty losses) that arises in a qualified disaster area on or after the first day of the incident period of the relevant qualified disaster and that is attributable to the qualified disaster.

Revenue Procedure 2018-8 provides safe-harbor methods that individual taxpayers can use in determining the amount of their casualty and theft losses for their personal-use residential real property and personal belongings. Additional safe-harbor methods are available in the case of casualty and theft losses occurring as a result of any federally declared disaster. The Service will not challenge an individual’s determination of the decrease in fair market value of personal-use residential real property or personal belongings if the individual qualifies for and uses one of the safe-harbor methods described in the Revenue Procedure. The Revenue Procedure is effective December 13, 2017.

Several key terms are defined in section 201 of the Taxpayer Certainty and Disaster Tax Relief Act. These are as follows:

  1. The term “incident period” with respect to any qualified disaster is the period specified by FEMA as the period during which the disaster occurred, except that the period cannot be treated as beginning before January 1, 2018, or ending after January 19, 2020 (the date that is 30 days after the date of enactment of the legislation).
  2. The term “qualified disaster zone” is the portion of the qualified disaster area determined by the President to warrant individual or individual and public assistance from the federal government under the Robert T. Stafford Disaster Relief and Emergency Assistance Act by reason of the qualified disaster with respect to the qualified disaster area.
  3. The term “qualified disaster area” is an area with respect to which the President declared a major disaster from January 1, 2018, through February 18, 2020 (the date that is 60 days after the date of enactment of the legislation), under section 401 of the Stafford Act if the incident period of the disaster began on or before December 20, 2019 (the date of enactment). To avoid providing double benefits, the legislation excludes the California wildfire disaster area, for which similar relief was provided by the Bipartisan Budget Act of 2018.
  4. “The term ‘qualified disaster’ means, with respect to any qualified disaster area, the disaster by reason of which a major disaster was declared with respect to such area.”

11. Those affected by qualified disasters can use prior-year earned income to determine their earned income tax credit and child tax credit.

Section 204(c) of the Taxpayer Certainty and Disaster Tax Relief Act of 2019 provides that a “qualified individual” can elect to use prior-year earned income for purposes of determining the individual’s earned income tax credit under section 32 and child tax credit under section 24. The election is available for qualified individuals whose earned income for the applicable tax year is lower than their earned income for the preceding tax year. A “qualified individual” is defined as an individual whose principal place of abode at any time during the incident period of any qualified disaster was located (1) in the qualified disaster zone with respect to the qualified disaster or (2) outside the qualified disaster zone, but within the qualified disaster area with respect to the disaster, if the individual was displaced from his or her principal place of abode by reason of the qualified disaster. The term “applicable tax year” is defined differently for qualified individuals in these two categories. For those in the first category (those within a qualified disaster zone), the applicable tax year is any taxable year date that includes any portion of the incident period of the qualified disaster. For those in the second category (those outside a qualified disaster zone who are displaced), the applicable tax year is any taxable year that includes any portion of the period during which they were displaced.

If a qualified individual makes this election, it applies for purpose of both the earned income tax credit and the child tax credit. For married couples filing a joint return, the election is available if either spouse is a qualified individual, and the earned income for the preceding year is the sum of the earned income in the preceding year of both spouses.

F. Divorce Tax Issues

There were no significant developments regarding this topic during 2019.

G. Education

1. Amounts can be withdrawn tax-free from section 529 accounts to pay expenses of apprenticeship programs and an aggregate amount of $10,000 can be withdrawn tax-free from section 529 accounts to repay qualified education loans of the beneficiary or a sibling.

Section 302 of the Setting Every Community Up for Retirement Enhancement Act of 2019 (SECURE Act) amended section 529 to add section 529(c)(8), which permits tax-free distributions from section 529 accounts to pay “expenses for fees, books, supplies, and equipment required for the participation of a designated beneficiary in an apprenticeship program” registered under the National Apprenticeship Act. The legislation also added section 529(c)(9), which permits tax-free distributions from section 529 accounts to pay “principal or interest on any qualified education loan (as defined in section 221(d)) of the designated beneficiary or a sibling of the designated beneficiary.” The limit on distributions for repayment of educational loans is an aggregate of $10,000. Amounts withdrawn to pay a sibling’s educational loans count against the sibling’s aggregate $10,000 limit, not the limit of the designated beneficiary. To the extent that amounts withdrawn tax-free from a section 529 account are used to pay interest on an educational loan, the taxpayer’s deduction for student loan interest under section 221 is reduced. These changes apply to distributions made after December 31, 2018.

H. Alternative Minimum Tax

There were no significant developments regarding this topic during 2019.

VI. Corporations

A. Entity and Formation

There were no significant developments regarding this topic during 2019.

B. Distributions and Redemptions

1. Now, this is “fake news” if we’ve ever heard it: The Service has ruled that a redemption which does not qualify under section 302 is a distribution under section 301. Duh!

For reasons we’re apparently too dense to understand, the Service has found it necessary to rule that a redemption by a C corporation that does not qualify under section 302 is treated as a distribution under section 301. Shocking! Okay, to be fair, Revenue Ruling 2019-13 also holds (not surprisingly) that if the C corporation’s nonqualifying redemption takes place during the corporation’s “post-termination transition period” (as defined in section 1377(b)) after converting from Subchapter S status, the distribution reduces the former S corporation’s accumulated adjustment account (AAA) before reducing earnings and profits (E&P) accumulated from prior C corporation years.

Facts. The facts set forth in Revenue Ruling 2019-13 are as follows: X was once a C corporation and later elected S status under section 1362(a). Then, X’s S election terminated under section 1362(d), such that it is now a C corporation. A, an individual, owns all 100 shares of the outstanding stock of X. At the time of its conversion to an S corporation, X had accumulated E&P of $600x and no current E&P. At the time of the termination of its S election, X’s AAA was $800x and its accumulated E&P was still $600x. During X’s post-termination transition period, X redeems 50 of A’s 100 shares of X stock for $1,000x. X makes no other distributions during the post-termination transition period. For the taxable period that includes the redemption, X has current E&P of $400x.

Law and Analysis: Recall that because A still owns 100% of the stock of X after the redemption, the transaction does not qualify for sale or exchange treatment under section 302 and therefore is treated as distribution under section 301. Further recall that the “post-termination transition period” under section 1377(b) generally is the one-year period following the termination of a corporation’s Subchapter S status. Under section 1371(e), any distribution of cash by a former S corporation with respect to its stock during the post-termination transition period ordinarily is applied against and reduces the adjusted basis of the recipient’s stock to the extent the distribution does not exceed the corporation’s AAA (within the meaning of section 1368(e)).

Held. The redemption of 50 of A’s 100 shares of X stock for $1,000x is characterized as a reduction of X’s $800x of AAA with the remaining $200x characterized as a dividend under section 301(c)(1).

2. Thirty years after the Technical and Miscellaneous Revenue Act of 1988, the Regulations under section 301 are proposed to be updated to make conforming changes.

The Technical and Miscellaneous Revenue Act of 1988 amended section 301(b)(1) and section 301(d), effective as if the amendments had been included in the Tax Reform Act of 1986, to eliminate certain distinctions that previously existed between corporate and noncorporate distributees and certain special rules for distributions to or from foreign corporations. As amended, these statutory provisions state that the amount of a corporate distribution is the amount of money received plus the fair market value of property received and that the basis of property received from a corporation is the fair market value of that property. Proposed Regulations update Regulation section 1.301-1 to reflect these changes and make certain nonsubstantive changes including modifying cross-references and reorganizing some provisions. Although the Proposed Regulations would be effective when published as final regulations, the statutory changes that they reflect are already effective.

3. Treasury and the Service have withdrawn the 2009 Proposed Regulations on allocation of consideration and allocation and recovery of basis in transactions involving corporate stock.

In 2009, the Treasury Department and the Service published Proposed Regulations under sections 301, 302, 304, 351, 354, 356, 358, 368, 861, 1001, and 1016 regarding the recovery of stock basis in (1) section 301 distributions and transactions that are treated as section 301 distributions and (2) sale and exchange transactions to which section 302(a) applies (including certain aspects of reorganization exchanges). The 2009 Proposed Regulations also provided the method for determining gain realized under section 356 and made a number of clarifying, but nonsubstantive, modifications to the rules for determining stock basis under section 358 resulting from a reorganization. The core principle underlying the rules was that each share of stock is a separate unit of property that can be sold or exchanged and the results of a transaction should be determined with respect to the consideration received in regard to each share. After considering comments submitted on these Proposed Regulations, the Treasury Department and the Service “determined that it is unlikely that the approach of the 2009 Proposed Regulations can be implemented in comprehensive final regulations without significant modifications.” Accordingly, the Treasury Department and the Service have withdrawn the 2009 Proposed Regulations and will continue to study the issues addressed in them “with a particular focus on issues surrounding sections 301(c)(2) and 304, and § 1.302-2(c) of the Income Tax Regulations.” The notice of withdrawal published in the Federal Register reiterates the belief of the Treasury Department and the Service in the core principle underlying the 2009 Proposed Regulations:

The Treasury Department and the IRS continue to believe that under current law, the results of a section 301 distribution should derive from the consideration received by a shareholder in respect of each share of stock, notwithstanding designations otherwise. See Johnson v. United States, 435 F.2d 1257 (4th Cir. 1971). The Treasury Department and the IRS also continue to believe that, under current law, with respect to redemptions governed by section 302(d), any unrecovered basis in the redeemed stock of a shareholder may be shifted to other stock only if such an adjustment is a proper adjustment within the meaning of [Regulation] § 1.302-2(c). Not all shifts of a redeemed shareholder’s unrecovered basis result in proper adjustments, and certain basis adjustments can lead to inappropriate results. See, e.g., Notice 2001-45, 2001-33 I.R.B. 129.

C. Liquidations

There were no significant developments regarding this topic during 2019.

D. S Corporations

1. A section 267 “looptrap” snares an accrual-method Subchapter S corporation with an ESOP shareholder.

In Petersen v. Commissioner, the taxpayers, a married couple, owned stock in an accrual-method S corporation with many employees. As permitted by section 1361(c)(7), an ESOP benefitting the employees also owned stock in the S corporation. The S corporation had accrued and deducted the following amounts with respect to its ESOP participants as of the end of its 2009 and 2010 tax years: for 2009, unpaid wages of $1,059,767 (paid by January 31, 2010) and vacation pay of $473,744 (paid by December 31, 2010); for 2010, unpaid wages of $825,185 (paid by January 31, 2011) and vacation pay of $503,896 (paid by December 31, 2011). Notwithstanding the fact that the S corporation was an accrual-method taxpayer, the Service asserted under section 267(a)(2) (forced matching) that the corporation was not entitled to deduct the foregoing accrued amounts until the year of actual payment and inclusion in gross income by the ESOP’s cash-method employee-participants.

In a case of first impression, the Tax Court (Judge Lauber) agreed with the Service based upon a plain reading of sections 67(a)(2), (b), and (e), as well as a determination that the S corporation’s ESOP is a “trust” within the meaning of section 267(c). Specifically, section 267(a)(2) generally requires so-called “forced matching” of an accrual-method taxpayer’s deductions with the gross income of a cash-method taxpayer to whom a payment is to be made if the taxpayer and the person to whom the payment is to be made are related persons as defined by section 267(b). For an S corporation, pursuant to section 267(e), all shareholders are considered related persons under section 267(b) regardless of how much or how little stock such shareholders actually or constructively own. Furthermore, under section 267(c) beneficiaries of a trust are deemed to own any stock held by the trust. Because the assets held by an ESOP are owned by a trust (as required by ERISA per 29 U.S.C. section 1103(a)), the participating employees of the ESOP are treated as shareholders of the S corporation. Hence, the forced-matching rule of section 267(a)(2) applies to accrued but unpaid wages and vacation pay owed to the S corporation’s ESOP participants at the end of the year.

Judge Lauber noted that this odd situation probably was a “drafting oversight”—in our words, a looptrap—because section 318, which defines related parties for certain purposes under Subchapter C, excepts tax-exempt employee trusts from its constructive ownership rules. Nevertheless, Judge Lauber wrote, the Tax Court is “not at liberty to revise section 267(c) to craft an exemption that Congress did not see fit to create.” Mercifully, however, the Tax Court declined to impose section 6662 negligence or substantial understatement penalties on the taxpayers because the case was one where “the issue was one not previously considered by the Court and the statutory language was not entirely clear” (even though the court obviously relied upon the plain language of section 267 to reach its decision).

a. This accrual-method S corporation was properly snared, says the Tenth Circuit. In an opinion by Judge Hartz, the Court of Appeals for the Tenth Circuit affirmed the Tax Court’s decision that an accrual-method S corporation’s deductions for amounts payable to cash-method participants in an ESOP that held shares of the S corporation were deferred by the forced-matching rule of section 267(a)(2). Section 267(a)(2) provides that the deductions of an accrual-method taxpayer for amounts payable to a related cash-method taxpayer must be deferred until the year in which the amounts are included in the related taxpayer’s gross income. Under section 267(c), beneficiaries of a trust are treated as constructively owning any stock held by the trust. Further, under section 267(e), all shareholders of an S corporation are treated as “related persons” within the meaning of section 267(b) regardless of how much or how little stock such shareholders actually or constructively own.

The Tenth Circuit agreed with the Tax Court that the effect of these provisions is that employees of an S corporation who participate in an ESOP that holds shares of the S corporation are “related persons” with respect to the S corporation within the meaning of section 267(b), and therefore an accrual-method S corporation’s deductions for amounts payable to such employees are subject to deferral under the forced-matching rule of section 267(a)(2). In reaching this conclusion, the court rejected several arguments made by the taxpayers and held that an ESOP is a “trust” within the meaning of section 267(c), and therefore the ESOP’s participants are treated as constructively holding proportionately the stock held by the ESOP.

2. In line with the continuing expansion of eligible shareholders of Subchapter S corporations, ESBTs now may have non-U.S. individuals as current beneficiaries.

Section 13541 of the TCJA made a technical change to section 1361(c)(2)(B)(v) such that for 2018 and future years an “electing small business trust” (ESBT), as particularly defined in section 1361(e), may have as a current beneficiary of the ESBT a “nonresident alien” individual. Under section 7701(b)(1)(B), a nonresident alien individual is a person who is neither a citizen nor a resident of the U.S. This change to section 1361 is permanent.

a. Final Regulations address the treatment of ESBTs that are S corporation shareholders and have nonresident aliens as beneficiaries. The Treasury Department and the Service have finalized without change Proposed Regulations addressing the treatment of ESBTs that are S corporation shareholders and have nonresident aliens as beneficiaries. The Preamble to the Proposed Regulations noted the apparent assumption in the legislative history of the TCJA that an ESBT is subject to tax and therefore would be subject to tax on the ESBT’s share of the S corporation’s income. That Preamble notes, however, that ESBTs can be grantor trusts for federal tax purposes with the result that the beneficiaries of the ESBT, not the ESBT itself, are subject to tax on the S corporation’s income. If a nonresident alien is a beneficiary of an ESBT, this could lead to the S corporation’s income not being subject to U.S. taxation (e.g., if the income is foreign-source). Therefore, according to the Preamble to the final Regulations, the final Regulations

modify the allocation rules under § 1.641(c)-1 to require that the S corporation income of the ESBT be included in the S portion of the ESBT if that income otherwise would have been allocated to an NRA [Non-Resident Alien] deemed owner under the grantor trust rules. Accordingly, such income will be taxed to the domestic ESBT by providing that, if the deemed owner is an NRA, the grantor portion of net income must be reallocated from the grantor portion of the ESBT to the ESBT’s S portion.

The final Regulations apply to all ESBTs after December 31, 2017.

3. If you’re a cash-method S corp pining to be a C corp, here’s your chance!

Section 13543 of the TCJA added new section 481(d) and new section 1371(f) to make it easier for cash-method S corporations to convert to C corporations (which typically, but not always, especially after the TCJA’s revisions to section 448, are accrual-method taxpayers). Specifically, new section 481(d) provides that any adjustment (such as changing from the cash to the accrual method) otherwise required under section 481(a)(2) with respect to an S to C conversion may be taken into account ratably over six years starting with the year of the change (instead of taking into account the adjustment entirely in the year of change) if three conditions are met: (1) the converting S corporation existed prior to December 22, 2017 (the date of the TCJA’s enactment); (2) the conversion from S to C status takes place prior to December 22, 2019 (two years from the date of the TCJA’s enactment); and (3) all of the shareholders of the S corporation on December 22, 2017, are “in identical proportions” the shareholders of the C corporation.

New section 1371(f) further provides that “money” distributed by the above-described converted S corporations after the “post-termination transition period” (generally one year) is allocable to and chargeable against the former S corporation’s AAA in the same ratio as AAA bears to accumulated E&P. Thus, new section 1371(f) is more favorable to S corporations converting to C status than the normal rule of section 1371(e), which allows distributions of money during the “post-termination transition period,” but not after, to be allocable to and chargeable against AAA. As a practical matter, then, S corporations converting to C corporations within the confines of new section 481(d) and section 1371(f) may make nontaxable, stock-basis reducing distributions of money out of their AAA during the one-year period following the conversion (pursuant to section 1371(e)) as well as wholly or partially (depending upon AAA as compared to E&P) nontaxable, basis-reducing distributions of money after the normal one-year, post-termination transition period. These changes to section 481 and section 1371 are permanent, but of course, will apply only to S to C conversions that meet the criteria of section 481(d) (i.e., pre-TCJA existing S corporations that convert to C status before December 22, 2019, and that have the same shareholders in the same proportions post-conversion).

a. Guidance concerning the adjustments required under new section 481(d). Revenue Procedure 2018-44 modifies Revenue Procedure 2018-31 to provide that an “eligible terminated S corporation,” as defined in section 481(d)(2), required to change from the overall cash method of accounting to an overall accrual method of accounting as a result of a revocation of its S corporation election, and that makes this change in method of accounting for the C corporation’s first taxable year after such revocation, is required to take into account the resulting positive or negative adjustment required by section 481(a)(2) ratably during the six-year period beginning with the year of change. Revenue Procedure 2018-44 also provides that an eligible terminated S corporation permitted to continue to use the cash method after the revocation of its S corporation election, and that changes to an overall accrual method for the C corporation’s first taxable year after such revocation, may take into account the resulting positive or negative adjustment required by section 481(a)(2) ratably during the six-year period beginning with the year of change.

b. Proposed Regulations for “ETSCs” issued just under the wire. As noted above, one of the requirements for “eligible terminated S corporation” status is conversion to C corporation status before December 22, 2019. For those S corporations that met the deadline and otherwise satisfied the above-mentioned requirements of section 481(d)—and who consequently have earned the new moniker “ETSCs”—the Treasury Department has issued further guidance in the form of Proposed Regulations. The Proposed Regulations were issued on November 7, 2019, beating the December 22, 2019, deadline by a little over a month. Whew!

Generally, the Proposed Regulations provide rules regarding (1) the definition of an ETSC, (2) distributions of money by an ETSC after the “post-termination transition period” (PTTP), and (3) the allocation of current C corporation current E&P to distributions of money and other property to the shareholders of ETSCs. The Proposed Regulations will apply to tax years beginning after the date that final regulations are published; however, the Proposed Regulations include a transition rule allowing corporations to apply certain existing regulations to distributions made after the PTTP but during open tax years (i.e., those tax years within the section 6511(a) claim for refund period). We commend these Proposed Regulations to further study by those tax advisers with affected clients.

4. We humbly ask, “Does it ever make sense to hold real estate in an S corporation?” And, “Will taxpayers ever learn that a series of ‘due tos’ and ‘due froms’ with related entities doesn’t amount to shareholder debt for purposes of Subchapter S?”

In Meruelo v. Commissioner, the taxpayer was a shareholder of an S corporation that suffered nearly a $27 million loss after banks foreclosed on its condominium complex. The taxpayer contended that he had sufficient basis in the S corporation’s indebtedness to him to absorb his $13 million share of the S corporation’s loss. According to the taxpayer, his basis stemmed from his $5 million capital contribution to the S corporation plus more than $9 million of net indebtedness owed to various other business entities in which the taxpayer owned an interest. Essentially, the $9 million of indebtedness for which the taxpayer claimed basis was derived from netting the S corporation’s accounts payable and accounts receivable with respect to other entities controlled by the taxpayer. The Service contended, however, that the taxpayer could claim only $5 million in losses because the net indebtedness owed by the S corporation to the taxpayer’s other business entities was not “bona fide indebtedness” that “runs directly” to the taxpayer. The Tax Court held in favor of the Service, upholding the Service’s asserted deficiency of approximately $2.6 million.

The Court of Appeals for the Eleventh Circuit, in an opinion by Judge Pryor, affirmed the Tax Court’s decision. Judge Pryor acknowledged, as did the Tax Court, that under the right circumstances either the “back-to-back” loan theory or the “incorporated pocketbook” theory argued by the taxpayer can support a taxpayer-shareholder’s claim of basis for S corporation debt owed to another party; however, the facts of the taxpayer’s case were nothing like the facts in cases premised upon the “back-to-back” loan theory or the “incorporated pocketbook” theory. There was no mention in Judge Pryor’s opinion of the Service’s assertion of accuracy-related penalties against the taxpayer. Perhaps the Service has a heart after all . . . .

E. Mergers, Acquisitions, and Reorganizations

1. Maybe Chubby Checker said it best: ♫♪Jack be nimble; Jack be quick. Jack go under [COI] limbo stick.♪♫

Among other requirements, shareholders of a target corporation must maintain a “substantial” proprietary interest (i.e., stock) in an acquiring corporation to qualify a transaction for tax-deferred reorganization treatment under section 368. The Regulations under section 368 set forth this shareholder continuity of interest (COI) test. The COI requirement is designed to prevent transactions that resemble sales from qualifying for tax-deferred reorganization treatment. Determining whether adequate COI exists for any particular transaction requires a comparison of the aggregate value of the target shareholders’ stock before the reorganization with the aggregate value of their stock held in the acquiring corporation after the reorganization. The required level of COI—jokingly, the “limbo stick”—varies in height depending upon the type of reorganization attempted (e.g., 50% safe harbor for straight and forward triangular mergers; 80% statutory requirement for reverse triangular mergers). Put differently, if boot in a reorganization is too high, the COI limbo stick is tripped, and the shareholders of the target corporation will not qualify for nonrecognition treatment. Thus, regardless of the type of reorganization attempted, valuation of the target shareholders’ pre- and post-reorganization stockholdings is critical for obtaining nonrecognition treatment.

Average trading price valuations allowed. Subject to other requirements and limitations, since 2011 the Treasury Department and the Service have permitted applicable COI tests to be met based upon actual trading values of publicly traded acquiror stock on either the closing date (as defined) or the signing date (as defined). Proposed Regulations promulgated in 2011 for publicly traded acquirors provide that, under specified circumstances, certain average trading price determinations of value are allowed for COI purposes. Commentators noted that average trading price methods often are used to determine the actual consideration paid by an acquiring corporation to target shareholders under acquisition agreements, so those same commentators argued that such average trading price methods should be acceptable for COI purposes in lieu of actual trading prices on either the closing date or signing date.

Revenue Procedure 2018-12 reflects the Treasury Department’s and the Service’s general agreement with the commentators that average trading price valuation methods are acceptable for COI purposes. The Revenue Procedure describes in detail the average trading price valuation methods that may be used for certain reorganization transactions. In particular, Revenue Procedure 2018-12 specifies that it applies to section 368(a)(1)(A) [mergers], (B) [stock for stock], (C) [stock for assets], and (G) [bankruptcy] reorganizations where the acquiring corporation is publicly traded. The safe-harbor valuation methods outlined in the Revenue Procedure are (1) the average of the daily volume-weighted average prices, (2) the average of the average high-low daily prices, and (3) the average of the daily closing prices. Of course, the specific requirements and limitations of Revenue Procedure 2018-12 are quite technical and must be carefully considered in connection with any potential reorganization transaction relying upon the Revenue Procedure for COI purposes. Nonetheless, the takeaway is that if one of the foregoing valuation methods is used to determine the stock consideration paid to target shareholders by a publicly traded acquiring corporation in one of the specified reorganizations, then such method generally may be used for COI purposes as well.

Revenue Procedure 2018-12 states that it applies only for COI purposes (not other valuation purposes) and that if the safe harbors of the Revenue Procedure are not met, the reorganization nevertheless may qualify for nonrecognition treatment under general federal tax principles. Finally, Revenue Procedure 2018-12 provides that the Service will entertain requests for rulings and determination letters that fall outside the scope of the Revenue Procedure.

a. Taxpayers have sufficient guidance on COI and the Proposed Regulations issued in 2011 are withdrawn. As indicated earlier, since 2011, final Regulations under section 368 generally have permitted the determination of whether the COI requirement is satisfied based on the actual trading value of a publicly traded acquiring corporation’s stock on either the closing date (as defined) or the signing date (as defined). Proposed Regulations promulgated in 2011 under section 368 provide in part that, under specified circumstances, certain average trading price determinations of value (rather than actual trading value on a specific date) are allowed for determining whether the COI requirement is satisfied.

The Treasury Department and the Service have concluded that current law generally provides sufficient guidance to taxpayers with respect to the COI requirement. Accordingly, the Proposed Regulations issued in 2011 have been withdrawn. However, because the Service also has concluded that taxpayers in certain circumstances should be able to rely on average stock valuation methods for purposes of measuring COI, the Service issued Revenue Procedure 2018-12, discussed above, which specifies the circumstances in which the Service will not challenge the use of certain average stock valuation methods in determining whether the COI requirement is satisfied.

2. Proposed Regulations address the items of income and deduction that are included in the calculation of built-in gains and built-in losses under section 382(h).

In an effort to minimize tax-motivated, tax-free acquisitions, Congress has enacted various provisions that limit an acquiring corporation’s ability to make use of an acquired corporation’s tax attributes, such as its net operating losses and tax credits. One such provision, section 382, in very simplified terms, limits an acquiring corporation’s ability to use an acquired corporation’s preacquisition net operating losses. Somewhat more accurately, section 382 limits the ability of a ‘‘loss corporation’’ to offset its taxable income in periods subsequent to an ‘‘ownership change’’ with losses attributable to periods prior to that ownership change. The section 382 limitation imposed on a loss corporation’s use of pre-change losses for each year subsequent to an ownership change generally is equal to the fair market value of the loss corporation immediately before the ownership change, multiplied by the applicable long-term tax-exempt rate as defined in section 382(f).

A loss corporation’s built-in gains and built-in losses affect its section 382 limitation. Section 382(h) provides rules relating to the determination of a loss corporation’s built-in gains and losses as of the date of the ownership change. Generally, built-in gains recognized during the five-year period beginning on the date of the ownership change allow a loss corporation to increase its section 382 limitation, and built-in losses recognized during this same period are subject to the loss corporation’s section 382 limitation. New Proposed Regulations address the items of income and deduction that are included in the calculation of built-in gains and losses under section 382 and reflect numerous changes made by the TCJA, which generated significant uncertainty regarding the application of section 382. The Preamble to the Proposed Regulations indicates that the Treasury Department and the Service propose to withdraw the following Service notices and incorporate their subject matter into the Proposed Regulations: Notice 87-79, Notice 90-29, Notice 2003-65, and Notice 2018-30. The proposed withdrawal of the prior Service notices would be effective on the day after the Proposed Regulations are published as final regulations in the Federal Register.

The Proposed Regulations generally would be effective for ownership changes occurring after the date on which they are published as final regulations in the Federal Register. However, taxpayers and their related parties (within the meaning of sections 267(b) and 707(b)(1)) may apply the Proposed Regulations to any ownership change occurring during a taxable year with respect to which the period described in section 6511(a) (the limitations period on refund claims) has not expired, as long as the taxpayers and all of their related parties consistently apply the rules of the Proposed Regulations to such ownership change and all subsequent ownership changes that occur before the effective date of the final regulations.

F. Corporate Divisions

1. The Service has suspended two old Revenue Rulings on the active trade or business requirement of sections 355(a)(1)(C) and (b).

If certain requirements are met, section 355(a)(1) permits a corporation to distribute stock and securities of a controlled corporation to its shareholders and security holders without recognizing gain or loss and without income to the recipients. One of those requirements is that the distributing corporation and the controlled corporation must be engaged in an active trade or business immediately after the distribution. To qualify, each trade or business must have been actively conducted throughout the five-year period ending on the date of the distribution. Under Regulation section 1.355-3(b)(2)(ii), a “trade or business” is “a specific group of activities . . . being carried on by the corporation for the purpose of earning income or profit, and the activities included in such group include every operation that forms a part of, or a step in, the process of earning income or profit.” The same Regulation further provides that “[s]uch group of activities ordinarily must include the collection of income and the payment of expenses.”

In Revenue Ruling 57-464 and Revenue Ruling 57-492, the Service concluded that certain activities conducted by a corporation did not meet the active trade or business requirement largely because the activities had failed to generate income. The Service has suspended these rulings pending the completion of a study by the Treasury Department and the Service. The study, which was previously announced in a statement on the Service website dated September 25, 2018, concerns

[possible] guidance to address whether a business can qualify as an [active trade or business] if entrepreneurial activities, as opposed to investment or other non-business activities, take place with the purpose of earning income in the future, but no income has yet been collected.

Pending completion of this study, the Service will entertain requests for private letter rulings regarding the qualification as an active trade or business of corporations that have not collected income.

A subsequent statement on the Service website dated May 6, 2019, requests information in a number of categories to assist the Service in identifying entrepreneurial activities that do not generate income but nevertheless should qualify as an active trade or business and explains the rationale for the study as follows:

In recent years, the IRS has observed a significant increase in entrepreneurial ventures that collect little or no income during lengthy and expensive R&D phases, particularly pharmaceutical and technology ventures. However, these types of ventures often use the R&D phase to develop new products that will generate income in the future but do not collect income during that phase. If a corporation wishes to achieve a corporate-level business purpose by separating one R&D segment from an established business or from another R&D segment, the IRS’s historical application of the income collection requirement likely would present a challenge for section 355 qualification.

2. Proposed Regulations provide guidance under section 355(e) regarding predecessors, successors, and limitation on gain recognition.

The Service has finalized Proposed and Temporary Regulations issued in 2016 under section 355(e) providing guidance to taxpayers in determining whether a corporation is a predecessor or successor of a distributing or controlled corporation for purposes of the gain-recognition exception under section 355(e). Generally, under section 355(a), in a spin-off or like transaction no gain or loss is recognized by a corporation (Distributing) that distributes the stock of a controlled corporation (Controlled) to Distributing’s shareholders. Similarly, nonrecognition is allowed under section 355(c) if certain “qualified property” is distributed from Distributing to its shareholders. Qualified property is generally defined by section 361(c) to include stock, stock rights, or obligations of either Distributing or Controlled. However, section 355(e) provides an exception to nonrecognition (requiring recognition of gain) where stock or securities are distributed by Controlled pursuant to a plan under which one or more persons acquires a 50% or greater interest (as defined in section 355(d)(4)(A)) in the stock of Distributing or Controlled. The general theory applied to transfers subject to section 355(e) is that gain recognition is appropriate if a distribution is effectuated to combine a tax-free division of the assets of a corporation other than Distributing or Controlled (divided corporation) with a planned acquisition of 50% or more of the divided corporation. Such transactions more closely resemble a corporate-level disposition of the portion of the business that is acquired. For these purposes, any predecessor or successor entity of either Controlled or Distributing is treated the same as and referred to as Controlled or Distributing.

The final Regulations add a new definition and detailed rules regarding the treatment of a Predecessor of Distributing (POD). To oversimplify, the final Regulations apply if there is a plan in place to acquire 50% or more of Distributing. Distributing will benefit from a gain limitation rule only if a POD exists and the POD does not also undergo a 50% acquisition pursuant to a plan. If no POD exists, then the gain must generally be recognized. If a POD exists but also undergoes a 50% acquisition pursuant to a plan, then Distributing must recognize gain with respect to acquisition of the POD (subject to certain gain limitation rules). The final Regulations apply to distributions occurring after December 15, 2019. For distributions occurring on or before December 15, 2019, a set of transition rules applies.

G. Affiliated Corporations and Consolidated Returns

There were no significant developments regarding this topic during 2019.

H. Miscellaneous Corporate Issues

1. Cash grants from the State of New Jersey were nontaxable contributions to capital, says the Tax Court.

The taxpayer in Brokertec Holdings, Inc. v. Commissioner was the common parent of a consolidated corporate group. Two members of the group were inter-dealer brokers with offices in or near the World Trade Center in New York City on September 11, 2001. Following the destruction of the World Trade Center in the September 11 terrorist attack, these members searched for new office space. They both applied for and received cash grants from the State of New Jersey’s Economic Development Plan. Both members relocated to areas of New Jersey adjacent to New York City. On the consolidated group’s returns for 2010 through 2013, a total of approximately $55.7 million of the cash grants were treated as nontaxable, nonshareholder contributions to capital under section 118. The Service asserted that the group was required to include the grants in gross income.

The Tax Court (Judge Jacobs) held that the grants were nontaxable contributions to capital. The court engaged in a lengthy review of prior cases that had addressed the issue of what constitutes a contribution to capital, including the Supreme Court’s decision in Brown Shoe Co. v. Commissioner, and the Third Circuit’s decision in Commissioner v. McKay Products. Corp. Based on this review, the court concluded that “the key to determining whether payments from a nonshareholder (here the State of New Jersey) are taxable to the recipient (here petitioner’s affiliates) or nontaxable as a contribution to capital is the intent or motive of the nonshareholder donor.” In this case, the court concluded, the intent of the State of New Jersey in making the grants was not to pay for services, but rather to induce the consolidated group members to establish their offices in a targeted area (known as an urban-aid municipality) both to bring in new jobs and to revitalize the area. “The facts in this case fall squarely within the four corners of section 1.118-1, Income Tax Regs., and are strikingly similar to those of Brown Shoe Co. and McKay Prods. Corp. . . . .” Accordingly, the court held, the grants were nontaxable, nonshareholder contributions to capital. Any appeal of the Tax Court’s decision by the government will be heard by the Court of Appeals for the Third Circuit, the same court that issued the opinion in McKay Prods. Corp.

Section 13312 of the TCJA amended section 118 effective after December 22, 2017, such that nonshareholder contributions to the capital of corporations made by governmental entities or civic groups no longer are excludable from the recipient corporation’s gross income. Accordingly, the result in this case would have been different if the years involved were subject to amended section 118.

VII. Partnerships

A. Formation and Taxable Years

There were no significant developments regarding this topic during 2019.

B. Allocations of Distributive Share, Partnership Debt, and Outside Basis

1. They were just kidding! Treasury and the Service have removed Temporary Regulations regarding the allocation of partnership liabilities for purposes of the section 707 disguised sale rules.

In 2016, the Treasury Department and the Service published Temporary Regulations (707 Temporary Regulations) regarding the allocation of partnership liabilities for purposes of applying the disguised sale rules of section 707. On April 21, 2017, President Trump issued Executive Order 13789 directing the Secretary of the Treasury to review “all significant tax regulations” issued on or after January 1, 2016, that “impose an undue financial burden,” “add undue complexity,” or “exceed [the Service’s] statutory authority,” and to submit two reports to the President. The second report, issued by Treasury Secretary Mnuchin on October 2, 2017, recommended certain actions with respect to eight sets of regulations, one of which was the 707 Temporary Regulations. The second report stated that the novel approach implemented in the 707 Temporary Regulations should be studied systematically and that the Treasury Department and the Service therefore would consider removing the 707 Temporary Regulations and reinstating prior regulations. The Treasury Department and the Service proposed removing the 707 Temporary Regulations in 2018 and now have done so.

The 707 Temporary Regulations Issued in 2016. Temporary Regulation section 1.707-5T(a)(2), published in 2016, provided that, for purposes of the disguised sale rules, a partner’s share of any partnership liabilities, regardless of whether they are recourse or nonrecourse under Regulation section 1.752-1 through 1.752-3, must be allocated by applying the same percentage used to determine the partner’s share of “excess nonrecourse liabilities” under Regulation section 1.752-3(a)(3), “but such share shall not exceed the partner’s share of the partnership liability under section 752 and applicable regulations (as limited in the application of section 1.752-3(a)(3) to this paragraph (a)(2)).” Regulation section 1.752-3(a)(3) (as amended in 2016) provided that, for purposes of the disguised sale rules of Regulation section 1.707-5(a)(2), a partner’s share of an excess nonrecourse liability is determined solely in accordance with the partner’s interest in partnership profits and that the significant item method, alternative method, and additional method do not apply. The combined effect of these rules was that, for purposes of the disguised sale rules, and regardless of whether a liability was recourse or nonrecourse, (1) a contributing partner’s share of a partnership liability was determined solely by the partner’s share of partnership profits and could not be determined either under the other methods normally authorized for allocating excess nonrecourse liabilities or with reference to that partner’s economic risk of loss under Regulation section 1.752-2 and (2) no portion of any partnership liability for which another partner bore the risk of loss could be allocated to the contributing partner under the profit-share method. The Treasury Department and the Service expressed the belief that, for purposes of the disguised sale rules, this allocation method reflected the overall economic arrangement of the partners. According to the Preamble to the 707 Temporary Regulations, “[i]n most cases, a partnership will satisfy its liabilities with partnership profits, the partnership’s assets do not become worthless, and the payment obligations of partners or related persons are not called upon.” These rules were designed to be the death knell of leveraged partnership disguised sale transactions à la Canal Corp. v. Commissioner, to which reference was made in the 2016 Preamble.

The Withdrawal of the 707 Temporary Regulations. The Treasury Department and the Service have now withdrawn the 707 Temporary Regulations and reinstated the rules under Regulation section 1.707-5(a)(2) as in effect prior to the 707 Temporary Regulations. Under these rules, (1) a partner’s share of a partnership’s recourse liability is the partner’s share of the liability under section 752 and the Regulations thereunder, i.e., recourse liabilities are allocated for purposes of the disguised sale rules under the normal rules for allocating recourse liabilities, and (2) nonrecourse liabilities are allocated by applying the same percentage used to determine the partner’s share of “excess nonrecourse liabilities” under Regulation section 1.752-3(a)(3), which means that a contributing partner’s share of a nonrecourse liability is determined for purposes of the disguised sale rules solely by the partner’s share of partnership profits and that the significant item method, alternative method, and additional method do not apply. The Regulations also reinstate the rule in former Regulation section 1.707-5(a)(2)(i) and (ii) for so-called section 1.752-7 contingent liabilities that a partnership liability is a recourse or nonrecourse liability to the extent that the obligation would be a recourse or a nonrecourse liability under Regulation sections 1.752-1(a)(1) and 1.752-1(a)(2), respectively, if the liability was treated as a partnership liability for purposes of section 752. The Preamble to the Proposed Regulations indicated that “[t]he Treasury Department and the Service continue to study the issue of the effect of contingent liabilities with respect to section 707, as well as other sections of the Code.” Finally, the Regulations reinstate Examples 2, 3, 7, and 8 under Regulation section 1.752-1-5(f) with a modification to the language in Example 3 to reflect an amendment made in 2016 to Regulation section 1.707-5(a)(3) regarding an anticipated reduction in a partner’s share of a liability that is not subject to the entrepreneurial risks of partnership operations.

Effective Date. The 707 Temporary Regulations expired on October 4, 2019. The amendments to Regulation section 1.707-5 apply to any transaction with respect to which all transfers occur on or after October 4, 2019. (These effective dates represent a change from the Proposed Regulations, which were proposed to apply 30 days following the date the Proposed Regulations were published as final regulations.) Nevertheless, taxpayers can apply these Regulations instead of the 707 Temporary Regulations to any transaction with respect to which all transfers occur on or after January 3, 2017.

2. Final Regulations address deficit restoration obligations, when partnership liabilities are treated as recourse liabilities, and bottom dollar guarantees.

The Treasury Department and the Service have finalized Proposed and Temporary Regulations that address when certain obligations to restore a deficit balance in a partner’s capital account are disregarded under section 704, when partnership liabilities are treated as recourse liabilities under section 752, and the treatment of so-called bottom dollar guarantees. The Proposed and Temporary Regulations were issued in 2016.

Background. Under Regulation section 1.752-1(a)(1), a partnership liability is recourse to the extent that any partner or related person bears the economic risk of loss (EROL) for the liability under Regulation section 1.752-2. Under Regulation section 1.752-2, a partner or related person bears the EROL to the extent the partner or related person would have a payment obligation if the partnership liquidated in a worst-case scenario in which all partnership liabilities are due and all partnership assets generally are worthless. For purposes of determining the extent to which a partner or related person has an obligation to make a payment, an obligation to restore a deficit capital account upon liquidation of the partnership under the section 704(b) Regulations is taken into account. Further, for this purpose, Regulation section 1.752-2(b)(6) presumes that partners and related persons who have payment obligations actually perform those obligations, irrespective of their net worth, unless the facts and circumstances indicate a plan to circumvent or avoid the obligation. Prior to these Regulations, this presumption was subject to an anti-abuse rule in Regulation section 1.752-2(j) pursuant to which a payment obligation of a partner or related person could be disregarded or treated as an obligation of another person if facts and circumstances indicated that a principal purpose of the arrangement was to eliminate the partner’s EROL with respect to that obligation or create the appearance of the partner or related person bearing the EROL when the substance was otherwise. This presumption was also subject to a disregarded-entity, net-value requirement under Regulation section 1.752-2(k) pursuant to which, for purposes of determining the extent to which a partner bears the EROL for a partnership liability, a payment obligation of a disregarded entity was taken into account only to the extent of the net value of the disregarded entity as of the allocation date.

2014 Proposed Regulations Under Section 752. In 2014, the Treasury Department and the Service issued proposed amendments to Regulation section 1.752-2 (2014 proposed amendments) providing that obligations to make a payment with respect to a partnership liability (excluding those imposed by state law) would not be recognized for purposes of section 752 unless certain recognition factors were present. These factors were intended to ensure that the terms of a payment obligation were not designed solely to obtain tax benefits. For example, one factor required a partner or related person to either maintain a commercially reasonable net worth during the term of the payment obligation or be subject to commercially reasonable restrictions on asset transfers for inadequate consideration. The 2014 proposed amendments to Regulation section 1.752-2 also provided generally that a payment obligation would be recognized only to the extent of the net value of a partner or related person as of the allocation date.

2016 Proposed Regulations Under Section 752. The 2016 Proposed Regulations partially withdrew the 2014 Proposed Regulations and adopted an approach that is now reflected, with some modifications, in the final Regulations.

Final Regulations Under Section 752. In response to comments expressing concern about the “all or nothing” approach of the 2014 Proposed Regulations, the final Regulations move the list of recognition factors to an anti-abuse rule in Regulation section 1.752-2(j)(3) (other than the recognition factors concerning bottom dollar guarantees and indemnities, which are addressed in concurrently issued final Regulations under section 752). Under the anti-abuse rule, the factors are weighed to determine whether a payment obligation (other than an obligation to restore a deficit capital account upon liquidation) should be respected. The list of factors in the anti-abuse rule is nonexclusive, and the weight to be given to any particular factor depends on the particular case. The final Regulations state that the presence or absence of any particular factor, in itself, is not necessarily indicative of whether or not a payment obligation is recognized under Regulation section 1.752-2(b). The final Regulations modify the recognition factors in various ways in response to comments on the 2014 and 2016 Proposed Regulations.

The 2016 Proposed Regulations also proposed to remove Regulation section 1.752-2(k), which provided that a payment obligation of a disregarded entity is taken into account only to the extent of the net value of the disregarded entity as of the allocation date, and proposed to create a new presumption under the anti-abuse rule in Regulation section 1.752-2(j). In contrast, the final Regulations retain Regulation section 1.752-2(k) but modify it to provide that an obligation of a partner or related person to make a payment is not recognized if the facts and circumstances indicate that there is not a reasonable expectation that the payment obligor will have the ability to make the required payments if the payment obligation becomes due and payable. For purposes of this rule, a payment obligor includes disregarded entities (including grantor trusts). The final Regulations contain two examples to illustrate the application of Regulation section 1.752-2(k).

Bottom Dollar Guarantees. Regulation section 1.752-2(b)(3) continues to provide that “[t]he determination of the extent to which a partner or related person has an obligation to make a payment under [Regulation] § 1.752-2(b)(1) is based on the facts and circumstances at the time of the determination,” and that “[a]ll statutory and contractual obligations relating to the partnership liability are taken into account.” However, the Regulation now carves out an exception under which “bottom dollar” guarantees and indemnities (or their equivalent, termed “bottom dollar payment obligations”) will not be recognized. According to Regulation section 1.752-2(b)(3)(ii)(C)(1), a bottom dollar payment obligation is a payment obligation that is the same or similar to one described in Regulation section 1.752-2(b)(3)(ii)(C)(1) as follows:

(i) With respect to a guarantee or similar arrangement, any payment obligation other than one in which the partner or related person is or would be liable up to the full amount of such partner’s or related person’s payment obligation if, and to the extent that any amount of the partnership liability is not otherwise satisfied.

(ii) With respect to an indemnity or similar arrangement, any payment obligation other than one in which the partner or related person is or would be liable up to the full amount of such partner’s or related person’s payment obligation, if, and to the extent that, any amount of the indemnitee’s or benefited party’s payment obligation that is recognized under this paragraph (b)(3) is satisfied.

(iii) With respect to an obligation to make a capital contribution or to restore a deficit capital account upon liquidation of the partnership as described in § 1.704-1(b)(2)(ii)(b)(3) …, any payment obligation other than one in which the partner is or would be required to make the full amount of the partner’s capital contribution or to restore the full amount of the partner’s deficit capital account.

(iv) An arrangement with respect to a partnership liability that uses tiered partnerships, intermediaries, senior and subordinate liabilities, or similar arrangements to convert what would otherwise be a single liability into multiple liabilities if, based on the facts and circumstances, the liabilities were incurred pursuant to a common plan, as part of a single transaction or arrangement, or as part of a series of related transactions or arrangements, and with a principal purpose of avoiding having at least one of such liabilities or payment obligations with respect to such liabilities being treated as a bottom dollar payment obligation.

As long as a partner or related person has a payment obligation that would be recognized but for the effect of an indemnity, reimbursement agreement, or similar arrangement, the payment obligation will be recognized under Regulation section 1.752-2(b)(3) if, taking into account the indemnity, reimbursement agreement, or similar arrangement, that partner or related person is liable for at least 90% of the initial payment obligation. Also, a payment obligation is not a bottom dollar payment obligation merely because a maximum amount is placed on the partner’s or related person’s payment obligation, a partner’s or related person’s payment obligation is stated as a fixed percentage of every dollar of the partnership liability to which such obligation relates, or there is a right of proportionate contribution running between partners or related persons who are co-obligors with respect to a payment obligation for which each of them is jointly and severally liable. Guarantees of a vertical slice of a partnership liability will be recognized.

Disclosure requirement. Regulation section 1.752-2(b)(3)(ii)(D) requires the partnership to disclose to the Service all bottom dollar payment obligations with respect to a partnership liability on a completed Form 8275, Disclosure Statement, attached to the partnership return for the taxable year in which the bottom dollar payment obligation is undertaken or modified.

Final Regulations Under Section 704. Prior to these amendments, the Regulations under Section 704 provided that a partner’s deficit restoration obligation was not respected if the facts and circumstances indicated a plan to circumvent or avoid the partner’s deficit restoration obligation. The final Regulations retain this rule in Regulation section 1.704-1(b)(2)(ii)(c)(4) and provide that a partner’s deficit restoration obligation also will not be respected if it is a bottom dollar payment obligation that is not recognized under Regulation section 1.752-2(b)(3). The final Regulations also add a nonexclusive list of factors to Regulation section 1.704-1(b)(2)(ii)(c)(4)(B) that are similar to the factors in the anti-abuse rule of Regulation section 1.752-2(j)(3). However, these factors are specific to deficit restoration obligations and are intended to indicate when a plan to circumvent or avoid a deficit restoration obligation exists. The weight to be given to any particular factor depends on the particular case and the presence or absence of any particular factor is not, in itself, necessarily indicative of whether or not the obligation is respected. The factors are: (1) the partner is not subject to commercially reasonable provisions for enforcement and collection of the obligation; (2) the partner is not required to provide (either at the time the obligation is made or periodically) commercially reasonable documentation regarding the partner’s financial condition to the partnership; (3) the obligation ends or could, by its terms, be terminated before the liquidation of the partner’s interest in the partnership or when the partner’s capital account as provided in Regulation section 1.704-1(b)(2)(iv) is negative other than when a transferee partner assumes the obligation; and (4) the terms of the obligation are not provided to all the partners in the partnership in a timely manner.

Effective Date. Subject to some exceptions, the final Regulations generally apply to liabilities incurred or assumed by a partnership and to payment obligations imposed or undertaken with respect to a partnership liability on or after October 9, 2019, other than liabilities incurred or assumed by a partnership and payment obligations imposed or undertaken pursuant to a written binding contract in effect prior to that date.

C. Distributions and Transactions Between the Partnership and Partners

1. No, you “May” not.

In July, 2019, the Treasury Department and the Service have finalized, with only minor, nonsubstantive changes, Temporary Regulation section 1.337(d)-3T, Temporary Regulation section 1.732-1T(c), and corresponding Proposed Regulations issued in 2015. These Regulations are intended to prevent a corporate partner from avoiding recognition under section 311(b) of corporate-level gain through transactions with a partnership involving equity interests of the corporate partner.

An example of this type of transaction—commonly called a “May Company” transaction—is as follows: A corporation enters into a partnership and contributes appreciated property. The partnership then acquires stock of that corporate partner, and later makes a liquidating distribution of this stock to the corporate partner. Under section 731(a), the corporate partner does not recognize gain on the partnership’s distribution of its stock. By means of this transaction, the corporation has disposed of the appreciated property it formerly held and acquired its own stock, permanently avoiding its gain in the appreciated property. If the corporation had directly exchanged the appreciated property for its own stock, section 311(b) would have required the corporation to recognize gain upon the exchange. Under the Regulations, if a transaction has the effect of an exchange by a corporate partner of its interest in appreciated property for an interest in stock of the corporate partner owned, acquired, or distributed by a partnership (a “Section 337(d) Transaction”), the corporate partner must recognize gain under a “deemed redemption” rule.

Deemed Redemption Rule. Under the deemed redemption rule, a corporate partner in a partnership that engages in a Section 337(d) Transaction must recognize gain at the time, and to the extent, that the corporate partner’s interest in appreciated property (other than stock of the corporate partner) is reduced in exchange for an increased interest in stock of the corporate partner. The complicated deemed redemption rule is triggered by the partnership’s purchase of stock of a corporate partner (or stock or other equity interests of any corporation that controls the corporate partner within the meaning of section 304(c), except that section 318(a)(1) and (3) do not apply for that purpose); gain recognition can be triggered without a subsequent distribution.

The Regulations provide general principles that apply in determining the amount of appreciated property effectively exchanged for stock of the corporate partner. The corporate partner’s economic interest with respect to both the stock of the corporate partner and all other appreciated property of the partnership must be determined based on all facts and circumstances, including the allocation and distribution rights set forth in the partnership agreement.

The gain from the hypothetical sale used to compute gain under the deemed redemption rule is determined by applying the principles of section 704(c). The corporate partner’s recognition of gain from a Section 337(d) Transaction triggers two basis adjustments. First, the partnership increases its adjusted basis in the appreciated property that is treated as the subject of a Section 337(d) Transaction by the amount of gain that the corporate partner recognizes with respect to that property as a result of the Section 337(d) Transaction regardless of whether the partnership has a section 754 election in effect. Second, the basis of the corporate partner’s interest in the partnership is increased by the amount of gain the corporate partner recognizes.

In limited circumstances, a partnership’s acquisition of stock of the corporate partner does not have the effect of an exchange of appreciated property for that stock. For example, if a partnership with an operating business uses the cash generated in that business to purchase stock of the corporate partner, the deemed redemption rule does not apply because the corporate partner’s share in appreciated property has not been reduced, and thus no exchange has occurred. The rules also do not apply if all interests in the partnership’s capital and profits are held by members of an affiliated group (defined in section 1504(a)) that includes the corporate partner.

Distribution of Corporate Partner’s Stock. A distribution of the corporate partner’s stock to the corporate partner by the partnership also can trigger gain recognition. In addition to any gain previously recognized under the deemed redemption rule, if stock of a corporate partner is distributed to the corporate partner, the corporate partner must recognize gain to the extent that the partnership’s basis in the distributed stock exceeds the corporate partner’s basis in its partnership interest (as reduced by any cash distributed in the transaction) immediately before the distribution.

De Minimis Exception. The rules described above do not apply if a de minimis exception is satisfied. The de minimis exception applies if three conditions are met: (1) the corporate partner and any related persons own less than five percent of the partnership; (2) the partnership holds stock of the corporate partner worth less than two percent of the value of the partnership’s gross assets, including stock of the corporate partner; and (3) the partnership has never, at any time, held more than $1 million in stock of the corporate partner or more than two percent of any particular class of stock of the corporate partner.

Effective Date. The final Regulations apply to transactions that occur on or after June 12, 2015.

a. We thought the final Regulations on partnership transactions involving equity interests of partners were already sufficiently complex. Proposed Regulations modify certain key definitions. Proposed Regulations modify certain definitions in the final Regulations that were issued in 2018 to address so-called “May Company” transactions. The deemed redemption rule in the final Regulations is triggered when a corporate partner exchanges an interest in appreciated property for an interest in “stock of the corporate partner” owned, acquired, or distributed by the partnership. The final Regulations generally define “stock of a corporate partner” as stock, or other equity interests, including options, warrants, and similar interests, in the corporate partner or a corporation that controls the corporate partner within the meaning of section 304(c) (except that section 318(a)(1) and (3) do not apply). The Proposed Regulations would make four amendments to the final Regulations.

First, the final Regulations excluded the attribution rules of section 318(a)(1) and (3) to limit for this purpose the meaning of control as defined in section 304(c) (generally stock possessing 50% or more of total combined voting power or value) to entities that own a direct or indirect interest in the corporate partner. Out of concern that excluding the attribution rules of section 318(a)(1) and (3) in determining control would allow taxpayers to structure transactions to eliminate gain on appreciated assets, the Proposed Regulations eliminate the exclusion of the attribution rules of section 318(a)(1) and (3) in determining control. Instead, according to the Preamble, the Proposed Regulations implement the rationale for the prior exclusion of the attribution rules more directly:

For the purpose of testing direct or indirect ownership of an interest in the Corporate Partner, ownership of Stock of the Corporate Partner would be attributed to an entity under section 318(a)(2) (except that the 50-percent ownership limitation in section 318(a)(2)(C) would not apply) and under section 318(a)(4), but otherwise without regard to section 318. Thus, sections 318(a)(1), 318(a)(3), and 318(a)(5) would not apply for determining whether an entity directly or indirectly owns an interest in Stock of the Corporate Partner, but once an entity is found to directly or indirectly own an interest in such stock, then the section 304(c) control definition would apply in its entirety to determine whether the tested entity is a Controlling Corporation.

Second, the Proposed Regulations would modify the rule in the 2018 final Regulations that stock of a corporate partner does not include any stock or equity interest held or acquired by a partnership if all interests in the partnership’s capital and profits are held by members of an affiliated group within the meaning of section 1504(a) (the “Affiliated Group Exception”). Out of concern that the Affiliated Group Exception may result in abuse, the Treasury Department and the Service propose to remove the Affiliated Group Exception from the Regulations and have requested comments describing situations in which a more tailored version of it might be appropriate.

Third, the Proposed Regulations would make certain modifications to the rule in the 2018 final Regulations that stock of the corporate partner includes interests in any entity to the extent that the value of the interest is attributable to stock of the corporate partner (the so-called value rule).

Finally, the Proposed Regulations would make certain conforming changes to the exception for certain dispositions of stock in Regulation section 1.337(d)-3(f)(2).

The Proposed Regulations would be effective on the date they are published as final regulations in the Federal Register, but taxpayers may rely on them for transactions occurring on or after June 12, 2015, provided that the taxpayer consistently applies the Proposed Regulations to such transactions.

D. Sales of Partnership Interests, Liquidations, and Mergers

1. The Tax Court gives the Service a lesson on the intersection of partnership and international taxation: subject to the exception in section 897(g), a foreign partner’s gain from the redemption of its interest in a U.S. partnership was not income effectively connected with the conduct of a U.S. trade or business.

In Grecian Magnesite Mining, Industrial & Shipping Co. v. Commissioner, the taxpayer, a corporation organized under the laws of Greece, held a 15% interest (later reduced to 12.6%) in Premier Chemicals, LLC, an LLC organized under Delaware law and classified for federal tax purposes as a partnership. The taxpayer accepted Premier’s offer to redeem its partnership interest and received a total of $10.6 million, half of which was paid in 2008 and half in January 2009. The taxpayer and Premier agreed that the payment in January 2009 was deemed to have been paid on December 31, 2008, and that the taxpayer would not share in any profits or losses in 2009. The taxpayer realized $1 million of gain from the 2008 redemption payment and $5.2 million from the 2009 redemption payment. The taxpayer filed a return on Form 1120-F for 2008 on which it reported its distributive share of partnership items, but did not report any of the $1 million realized gain from the 2008 redemption payment. The taxpayer did not file a U.S. tax return for 2009 and thus did not report any of the $5.2 million realized gain from the 2009 redemption payment.

The Service issued a notice of deficiency in which it asserted that all of the $6.2 million of realized gain was subject to U.S. tax because it was U.S.-source income effectively connected with the conduct of a U.S. trade or business. The taxpayer conceded that $2.2 million of the gain was subject to U.S. taxation pursuant to section 897(g), which treats amounts received by a foreign person from the sale or exchange of a partnership interest as amounts received from the sale or exchange of U.S. real property to the extent the amounts received are attributable to U.S. real property interests. The taxpayer’s concession left $4 million of realized gain in dispute.

The Tax Court (Judge Gustafson) held that the $4 million of disputed gain was not income effectively connected with the conduct of a U.S. trade or business and therefore was not subject to U.S. taxation. In reaching this conclusion, the court addressed several issues. The court first analyzed the nature of the gain realized by the taxpayer. Under section 736(b)(1), payments made in liquidation of the interest of a retiring partner that are made in exchange for the partner’s interest in partnership property are treated as a distribution to the partner. Treatment as a distribution triggers section 731(a)(1), which provides that a partner recognizes gain from a distribution to the extent the amount of money received exceeds the partner’s basis in the partnership interest and directs that the gain recognized “shall be considered as gain or loss from the sale or exchange of the partnership interest of the distributee partner.” Pursuant to section 741, gain recognized from the sale or exchange of a partnership interest is “considered as gain or loss from the sale or exchange of a capital asset” except to the extent provided by section 751. The taxpayer asserted that these provisions lead to the conclusion that the taxpayer’s gain must be treated as arising from the sale of a single asset, its partnership interest, which is a capital asset. The government argued that the taxpayer’s gain must be treated as arising from the sale of separate interests in each asset owned by the partnership. Otherwise, the government argued, the rule in section 897(g), which imposes U.S. tax to the extent amounts received from the sale of a partnership interest are attributable to U.S. real property interests, would be rendered inoperable. The court agreed with the taxpayer. Section 897(g), the court explained,

actually reinforces our conclusion that the entity theory is the general rule for the sale or exchange of an interest in a partnership. Without such a general rule, there would be no need to carve out an exception to prevent U.S. real property interests from being swept into the indivisible capital asset treatment that section 741 otherwise prescribes.

The court noted that this conclusion was consistent with the court’s prior decision in Pollack v. Commissioner.

The court next addressed whether the $4 million of disputed gain was effectively connected with the taxpayer’s conduct of a U.S. trade or business. Pursuant to section 875(1), the taxpayer was considered to be engaged in a U.S. trade or business because the partnership of which it was a partner, Premier, was engaged in a U.S. trade or business. Accordingly, the issue was narrowed to whether the disputed gain was effectively connected with that trade or business. Because foreign-source income is considered effectively connected with a U.S. trade or business only in narrow circumstances, which the Service acknowledged were not present, the taxpayer’s disputed gain could be considered effectively connected income only if it was U.S.-source income. Pursuant to the general rule of section 865(a), income from the sale of personal property by a nonresident is foreign-source income. Nonetheless, the Service asserted that an exception in section 865(e)(2)(A) applied (the “U.S. office rule”). Under the U.S. office rule, if a nonresident maintains an office or other fixed place of business in the United States, income from a sale of personal property is U.S.-source if the sale is attributable to that office or fixed place of business. The court assumed without deciding that Premier’s U.S. office would be attributed to the taxpayer under section 864(c)(5). Accordingly, the issue was whether the gain was attributable to Premier’s U.S. office. Under section 864(c)(5)(B), income is attributable to a U.S. office only if the U.S. office is a material factor in the production of the income and the U.S. office “regularly carries on activities of the type from which such income, gain, or loss is derived.” The court concluded that neither of these requirements was satisfied. The court examined Regulation section 1.864-6(b)(2)(i) and concluded that, although Premier’s business activities might have had the effect of increasing the value of the taxpayer’s partnership interest, those business activities did not make Premier’s U.S. office a material factor in the production of the taxpayer’s gain. Further, the court concluded that, even if the U.S. office was a material factor, Premier did not regularly carry on activities of the type from which the gain was derived because “Premier was not engaged in the business of buying or selling interests in itself and did not do so in the ordinary course of business.” Because the disputed gain was not U.S.-source income, it was not effectively connected with the conduct of a U.S. trade or business and therefore not subject to U.S. taxation.

In reaching its conclusion that the taxpayer’s gain was not effectively connected with the conduct of a U.S. trade or business, the court rejected the Service’s contrary conclusion in Revenue Ruling 91-32. In that Ruling, according to the court, the Service concluded

that the gain realized by a foreign partner upon disposing of its interest in a U.S. partnership should be analyzed asset by asset, and that, to the extent the assets of the partnership would give rise to effectively connected income if sold by the entity, the departing partner’s pro rata share of such gain should be treated as effectively connected income.

The court characterized the analysis in the ruling as “cursory” and declined to follow it.

Although the taxpayer should have reported some of its gain in 2008, should have filed a 2009 U.S. tax return reporting gain in 2009, and should have paid tax with respect to both years because all of the gain realized from the 2008 distribution and some of the gain realized from the 2009 distribution was attributable to U.S. real property interests held by the U.S. partnership, Premier, the court declined to impose either the failure-to-file penalty of section 6651(a)(1) or the failure-to-pay penalty of section 6651(a)(2) because the taxpayer had relied on the advice of a CPA and, therefore, in the court’s view, established a reasonable cause, good faith defense.

a. Grecian Magnesite may have won the battle, but the Service has won the war with respect to a non-U.S. partner’s sale of an interest in a partnership doing business in the U.S. (thereby codifying the Service’s position in Revenue Ruling 91-32). Section 13501 of the TCJA amended section 864(c) by adding section 864(c)(8). New section 864(c)(8) provides that, effective for dispositions after November 27, 2017, gain or loss on the sale or exchange of all (or any portion) of a partnership interest owned by a nonresident alien individual or a foreign corporation in a partnership engaged in any trade or business within the U.S. is treated as effectively connected with a U.S. trade or business (and therefore taxable by the U.S. unless provided otherwise by treaty) to the extent that the transferor would have had effectively connected gain or loss had the partnership sold all of its assets at fair market value as of the date of the sale or exchange. The amount of gain or loss treated as effectively connected under this rule is reduced by the amount of such gain or loss that is already taxable under section 897 (relating to U.S. real property interests). Section 13501 of the TCJA makes corresponding changes to the withholding rules for effectively connected income under section 1446. These changes to section 864(c) and section 1446 statutorily reversed the Tax Court’s decision in Grecian Magnesite and effectively adopt the Service’s position in Revenue Ruling 91-32.

b. Temporary guidance on new withholding rules with respect to dispositions of partnership interests by non-U.S. partners, but publicly traded partnerships get a “temporary” pass. Section 13501 of the TCJA added new section 1446(f) to require that when section 864(c)(8) applies the transferee of a non-U.S. partner’s partnership interest must withhold, report, and pay over a tax equal to ten percent of the amount realized upon the disposition (unless specified exceptions apply) effective for transfers after December 31, 2017. Practitioners objected to immediate implementation of the new withholding rules, pointing out that without forms, instructions, or other guidance, it was unclear when or how to deposit the withheld amounts. To address these concerns, Notice 2018-29 provides interim guidance on reporting and paying over the amount required to be withheld under section 1446(f)(1).

Notice 2018-29 should be consulted by taxpayers affected by new section 864(c)(8), but generally speaking, the temporary guidance adopts the forms and procedures relating to withholding on dispositions of U.S. real property interests under section 1445 and the Regulations thereunder. With respect to publicly traded partnerships, however, Notice 2018-8 announces that the Treasury Department and the Service have determined that withholding under new section 1446(f) is not required with respect to any disposition of an interest in a publicly traded partnership (within the meaning of section 7704(b)) until regulations or other guidance have been issued. Notice 2018-8 emphasizes that this temporary suspension is limited to dispositions of interests that are publicly traded and does not extend to nonpublicly traded interests.

c. Proposed Regulations implementing new section 864(c)(8) issued. The Treasury Department and the Service have issued Proposed Regulations that implement new section 864(c)(8). As required by section 864(c)(8), the Proposed Regulations adopt a two-part analysis for determining effectively connected income or loss upon a foreign partner’s sale or exchange of its partnership interest. First, section 864(c)(8)(A) requires a foreign partner to apply the normal rules of Subchapter K to determine its overall gain or loss (including ordinary income or loss from “hot assets” under section 751) on the transfer of a partnership interest (“outside gain” and “outside loss”). Second, the outside gain or outside loss is compared to amounts determined under section 864(c)(8)(B), which can limit otherwise reportable effectively connected income or loss of the foreign partner. Consistent with the Service’s position in Grecian Magnesite and Revenue Ruling 91-32, section 864(c)(8)(B) uses a hypothetical partnership level sale or exchange analysis to derive inside “aggregate deemed sale EC capital gain,” “aggregate deemed sale EC capital loss,” “aggregate deemed sale EC ordinary gain,” and “aggregate deemed sale EC ordinary loss.” Outside gain or loss determined under section 864(c)(8)(A) then is compared to inside gain or loss determined under section 864(c)(8)(B) to derive the amount ultimately reportable by the foreign partner as effectively connected income or loss upon the sale or exchange of its partnership interest. Thus, for example, a foreign partner would compare its outside capital gain to its aggregate deemed sale EC capital gain, treating the former as effectively connected gain only to the extent it does not exceed the latter. The Proposed Regulations provide several examples illustrating the application of new section 864(c)(8). The Proposed Regulations do not, however, address the corresponding modifications to the withholding rules in section 1446(f), stating only that the latter regulations are to be issued “expeditiously.”

d. A victory in the D.C. Circuit for the taxpayer, but merely a pyrrhic victory (see above) for future, similarly-situated taxpayers. The Court of Appeals for the District of Columbia Circuit, in an opinion by Judge Srinivasan, has upheld the Tax Court’s decision that the $4 million of disputed gain at issue in Grecian Magnesite before the Tax Court was not effectively connected income by virtue of the U.S. office rule in section 865(e)(2)(A). In reaching its decision, the D.C. Circuit assumed without deciding, as did the Tax Court, that Premier’s U.S. office would be attributed to the taxpayer under section 864(c)(5). Further, the D.C. Circuit agreed with the Tax Court that little deference should be given to the Service’s position espoused in Revenue Ruling 91-32—that gain realized by a foreign partner from the disposition of an interest in a U.S. partnership should be analyzed on an asset-by-asset basis. The Service made a technical argument that the Tax Court’s decision was incorrect under canons of statutory interpretation, but the D.C. Circuit relied on competing canons of statutory interpretation to side with the taxpayer.

E. Inside Basis Adjustments

There were no significant developments regarding this topic during 2019.

F. Partnership Audit Rules

There were no significant developments regarding this topic during 2019.

G. Miscellaneous

1. Nonowner contributions to the capital of partnerships and LLCs taxed as partnerships are not excludable, and the common law contribution to capital doctrine is on life support if not dead.

Section 13312 of the TCJA amended section 118 effective after December 22, 2017, such that nonshareholder contributions to the capital of corporations made by governmental entities or civic groups are no longer excludable from the recipient corporation’s gross income. Previously, such capital contributions were nontaxable, and they occasionally were made to incentivize corporations either to locate in particular communities or to acquire or redevelop distressed property in a community (or do both). In addition, the Conference Report accompanying the changes to section 118, along with the cases summarized below, probably leads to the conclusion that similarly-motivated capital contributions to noncorporate entities (i.e., partnerships and LLCs taxed as partnerships) are no longer excludable from gross income (if they ever were), even though such contributions are outside the purview of either old or amended section 118.

a. No good deed goes unpunished. In Ginsburg v. United States, the Court of Federal Claims held that the State of New York’s payment of approximately $1.8 million to an LLC (taxed as a partnership) to incentivize and reward redevelopment of brownfield property is includable in the taxpayer-member’s gross income. The taxpayer owned 90% of an LLC taxed as a partnership for federal income tax purposes. The taxpayer’s LLC participated in New York’s Brownfield Development Tax Credit program in connection with acquiring an abandoned shoe factory in 2004 and eventually restoring it as a 134-unit residential building by 2011. New York’s Brownfield Tax Credit program allows certain credits against state income taxes based on investment in qualifying brownfield property. Further, if the credit is fully used by a taxpayer to offset applicable New York state income taxes, the excess of the credit over the amount used against state income taxes is paid to the taxpayer. Accordingly, after certifying that the taxpayer’s LLC had complied with the terms of the Brownfield Development Tax Credit program, New York paid the taxpayer’s LLC approximately $1.8 million in 2013 in satisfaction of the taxpayer’s excess credit amount. The taxpayer took the position on his 2013 federal income tax return that his 90% allocable share of the $1.8 million payment was excludable from gross income as a nontaxable capital contribution to the LLC. (New York law allowed exclusion of the payment for New York income tax purposes.) Upon audit, the Service determined that the payment constituted gross income to the LLC and thus to the taxpayer as part of his allocable share of partnership income. This adjustment resulted in additional gross income to the taxpayer for 2013 and a corresponding underpayment of approximately $602,000. The taxpayer paid the underpayment, filed a refund claim, and then brought this action in the Court of Federal Claims.

Analysis: Upon cross-motions for summary judgment, the Court of Federal Claims (Judge Hodges) agreed with the government that the $1.8 million constituted gross income to the taxpayer’s LLC and thereby to the taxpayer. The government had argued, and the court agreed, that the payment was includable by the broad terms of section 61(a) (gross income from whatever source derived) and that no statutory exclusions or exceptions applied. The taxpayer argued unsuccessfully that the $1.8 million payment was (1) a nontaxable contribution to the LLC’s capital, (2) a nontaxable recovery of the LLC’s investment in the brownfield project owned by the LLC, or (3) a nontaxable state “general-welfare” grant to the LLC. The taxpayer acknowledged that under any of the above theories the taxpayer’s basis in the brownfield project would be adjusted downward by the amount excludable. Judge Hodges reasoned that, because the taxpayer could not point to an express provision of the Code to support his nontaxable contribution to capital theory, no such exclusion applied. Furthermore, Judge Hodges reasoned that the payment to the partnership could not be a recovery of the LLC’s investment in the project because the payment came from a third party (the State of New York), not from the seller of the property. Judge Hodges expressed the view that the recovery of capital doctrine applies only in the context of buyers and sellers of “goods,” and in that context, a payment can be nontaxable as a purchase price adjustment. Finally, Judge Hodges determined that New York’s payment to the taxpayer’s LLC did not qualify for the “general-welfare” exclusion recognized in Revenue Ruling 2005-46 because the tax credit in question was not conditioned on a showing of need.

The holding of the Court of Federal Claims regarding the unavailability of the general-welfare exclusion is consistent with the Tax Court’s holding in Maines v. Commissioner. In Maines, the Tax Court held that the refundable portions of certain New York targeted economic development credits that remained after first reducing state tax liability were accessions to the taxpayers’ wealth and were includable in gross income under section 61 for the year in which the taxpayers received payment or, under the constructive receipt doctrine, were entitled to receive payment, even if they elected to carry forward the credit. The Tax Court concluded that the taxpayers could not exclude the payments under the general-welfare exclusion because the payments were not conditioned on a showing of need.

b. Yet again, no good deed goes unpunished. But perhaps there could have been a workaround? In Uniquest Delaware, LLC v. United States, the District Court for the Western District of New York held that a grant paid by the New York State Empire State Development Corporation (which appears to have been a government-funded corporation) to an LLC taxed as a partnership was not excludable from the LLC’s gross income as a contribution to capital. The taxpayer in this case was the LLC (unlike in Ginsburg in which the taxpayer was a partner-member of the LLC). The LLC, a TEFRA partnership, had two equal members, each of which was a disregarded single-member LLC, that in turn were each wholly-owned by separate Subchapter S corporations. The case arose in connection with a TEFRA-partnership audit of the LLC, a fact which was important to the court’s ultimate decision (as explained further below). In 2009, the LLC received an $11 million grant from the Empire State Development Corporation for the restoration of a building in Buffalo. The original grant proposal expressly stated that “[t]here is no element of compensation of specific, quantifiable or other services to the government agencies involved; the grants contemplated by this offer are being offered solely for the purpose of obtaining an advantage for the general community.” The LLC did not include the $11 million grant in its income on its partnership tax return for 2009. During the audit and at IRS Appeals, the Service asserted that the $11 million grant was included in the LLC’s gross income in 2009 and ultimately issued a final partnership administrative adjustment (FPAA) accordingly. The taxpayer-LLC then sought judicial review of the FPAA in federal district court.

Analysis. As in Ginsburg, the Service’s argument in this case was simple: section 61(a) requires inclusion of the $11 million grant in gross income, and no exception or exclusion in the Code provides otherwise. The taxpayer-LLC, similar to the taxpayer in Ginsburg, argued alternatively that the $11 million grant was either (1) excludable under the “common law contribution to capital doctrine” or (2) akin to a “rebate” that resulted in an adjustment to the taxpayer-LLC’s basis in the building, but which was not includable in gross income. Judge Wolford ruled against the taxpayer-LLC with respect to both arguments. Regarding the taxpayer-LLC’s “common law contribution to capital doctrine” argument, the court reasoned that the cases supporting the doctrine involved corporate taxpayers only, and the holdings in these cases were codified by section 118 (the pre-TCJA version), which expressly does not apply to noncorporate entities. Regarding the taxpayer-LLC’s “rebate” argument, Judge Wolford ruled that the $11 million grant is distinguishable, stating

unlike a retail customer who purchases a car with the knowledge that a rebate is forthcoming, [the taxpayer] purchased the [Buffalo Building] and then subsequently sought and received the [$11 million grant]. Therefore, the [$11 million grant] cannot be considered a discount or reduction in the purchase price of the building.

Indirect sections 118 and 702 Argument. The taxpayer-LLC argued that, even if section 118 applies only to corporations, the court should indirectly rule it applicable to resolve the dispute with the Service because the ultimate owners of the taxpayer-LLC were Subchapter S corporations. The taxpayer further argued in this regard that section 118 (pre-TCJA) would have allowed the S corporation members of the taxpayer-LLC to exclude the grant from gross income. Therefore, the taxpayer-LLC argued, if the S corporation members could have excluded the grant under section 118, then the grant ultimately should be held nontaxable by virtue of section 702’s distributive share approach to partner-level income. With respect to this final argument, Judge Wolford ruled that because TEFRA audit procedures treat the taxpayer-LLC as an entity separate from its owners the partner-level treatment by the ultimate owners of the LLC was not within the court’s subject-matter jurisdiction.

Planning pointer. Had the Subchapter S corporations first received the $11 million grant from New York and then contributed the funds to the taxpayer-LLC as additional capital contributions, we believe the grant would not have been taxable pursuant to the pre-TCJA version of sections 118 and 721, respectively. On the other hand, perhaps the terms of the grant would not allow the funds to be paid to the S corporation members because the acquisition and development was performed by the taxpayer-LLC, not the S corporation members.

c. The Federal Circuit has affirmed the Claims Court’s decision that an LLC classified as a tax partnership could not exclude from gross income a cash payment received from the State of New York. In Ginsburg v. United States, the taxpayer owned 90% of an LLC taxed as a partnership for federal income tax purposes. The taxpayers held 90% of the membership interests in an LLC that participated in New York’s Brownfield Development Tax Credit program in connection with acquiring an abandoned shoe factory in 2004 and eventually restoring it as a 134-unit residential building by 2011. Under this program, if the credit is fully used by a taxpayer to offset applicable New York state income taxes, the excess of the credit over the amount used against state income taxes is paid to the taxpayer. After certifying that the taxpayers’ LLC had complied with the terms of the Brownfield Development Tax Credit program, in 2013 New York paid the taxpayer’s LLC approximately $1.8 million in satisfaction of the taxpayer’s excess credit amount. The taxpayers took the position on their 2013 federal income tax return that their 90% allocable share of the $1.8 million payment was excludable from gross income as a nontaxable capital contribution to the LLC. Following an audit, the taxpayers paid the underpayment asserted by the Service of approximately $602,000, filed a refund claim, and then brought a refund action in the Court of Federal Claims, which held that the payment constituted gross income.

On appeal, the Court of Appeals for the Federal Circuit (Judge Wallach) affirmed the decision of the Court of Federal Claims granting summary judgment to the government and held that an LLC classified as a partnership had to include in gross income a cash payment received from the State of New York. As a result, the members of the LLC, including the taxpayers in this case, had to include their distributive shares of the payment in gross income. The Federal Circuit first concluded that the funds received were an economic gain over which the taxpayers had complete dominion and therefore constituted gross income under Commissioner v. Glenshaw Glass Co. The court rejected all of the taxpayer’s arguments that the payments were excludable from income, including arguments that (1) the payment for the excess amount was a nontaxable return of capital and (2) the brownfield redevelopment tax credit was “‘indistinguishable from . . . inducement payments, rebates, and reimbursements that’ have historically been treated as ‘not includable in gross income.’”

2. Relief for not reporting negative tax capital accounts.

The updated 2018 Instructions for Form 1065 and accompanying Schedule K-1 now require a partnership that does not report tax basis capital accounts to its partners to report, on line 20 of Schedule K-1 (Form 1065) using code AH, the amount of a partner’s tax basis capital both at the beginning of the year and at the end of the year if either amount is negative. Aware that some taxpayers and their advisers may not have been prepared to comply with this new requirement for 2018 returns, the Service, in Notice 2019-20, has provided limited relief. Specifically, the Service will waive penalties under (1) section 6722 for failure to furnish a partner a Schedule K-1 (Form 1065) and section 6698 for failure to file a Schedule K-1 (Form 1065) with a partnership return, (2) section 6038 for failure to furnish a Schedule K-1 (Form 8865), and (3) any other section of the Code for failure to file or furnish a Schedule K-1 or any other form or statement, for any penalty that arises solely as a result of failing to include negative tax basis capital account information provided the following conditions are met:

1. The Schedule K-1 or other applicable form or statement is timely filed, including extensions, with the IRS; is timely furnished to the appropriate partner, if applicable; and contains all other required information.

2. The person or partnership required to file the Schedule K-1 or other applicable form or statement files with the IRS, no later than one year after the original, unextended due date of the form to which the Schedule K-1 or other applicable form or statement must be attached, a schedule setting forth, for each partner for which negative tax basis capital account information is required:

a. the partnership’s name and Employer Identification Number, if any, and Reference ID Number, if any;

b. the partner’s name, address, and taxpayer identification number; and

c. the amount of the partner’s tax basis capital account at the beginning and end of the tax year at issue.

The above-described supplemental schedule should be captioned “Filed Under Notice 2019-20” in accordance with instructions and additional guidance posted by the Service on www.IRS.gov. The due date for this supplemental schedule is determined without consideration of any extensions, automatic or otherwise, that may apply to the due date for the form itself. Furthermore, the schedule should be sent to the address listed in the Notice, and the penalty relief applies only for taxable years beginning after December 31, 2017, but before January 1, 2019.

a. The Service has issued FAQ guidance on negative tax basis capital account reporting. The Service has issued guidance on the requirement to report negative tax basis capital account information in the form of frequently asked questions (FAQs) on its website.

Definition and calculation of tax basis capital accounts. In the FAQs, the Service explains that “[a] partner’s tax basis capital account (sometimes referred to simply as ‘tax capital’) represents its equity as calculated using tax principles, not based on GAAP, § 704(b), or other principles.” The FAQs provide guidance on the calculation of a partner’s tax basis capital account. A partner’s tax basis capital account is increased by the amount of money and the adjusted basis of any property contributed by the partner to the partnership (less any liabilities assumed by the partnership or to which the property is subject) and is decreased by the amount of money and the adjusted basis of any property distributed by the partnership to the partner (less any liabilities assumed by the partner or to which the property is subject). The partner’s tax basis capital account is increased by certain items, such as the partner’s distributive share of partnership income and gain, and is decreased by certain items, such as the partner’s distributive share of partnership losses and deductions. The FAQs make clear that a partner’s tax basis capital account is not the same as a partner’s basis in the partnership interest (outside basis) because outside basis includes the partner’s share of partnership liabilities, whereas a partner’s tax basis capital account does not.

Effect of section 754 Elections and Revaluations of Partnership Property. If a partnership has a section 754 election in effect, then it increases or decreases the adjusted basis of partnership property pursuant to section 743(b) when there is a transfer of a partnership interest or pursuant to section 734(b) when there is a distribution by the partnership. These adjustments can also be triggered when the partnership does not have a section 754 election in effect but has a substantial built-in loss and a transfer of a partnership interest occurs (section 743(b) basis adjustment) or experiences a substantial basis reduction in connection with a distribution (section 734(b) basis adjustment). The FAQs clarify that a partner’s tax basis capital account is increased or decreased by a partner’s share of basis adjustments under section 743(b) and section 734(b). In contrast, according to the FAQs, revaluations of partnership property pursuant to section 704 (such as upon the entry of a new partner) do not affect the tax basis of partnership property or a partner’s tax basis capital account.

Examples. The FAQs provide the following examples of the calculation of a partner’s tax basis capital account:

Example 1: A contributes $100 in cash and B contributes unencumbered, nondepreciable property with a fair market value (FMV) of $100 and an adjusted tax basis of $30 to newly formed Partnership AB. A’s initial tax basis capital account is $100 and B’s initial tax basis capital account is $30.
Example 2: The facts are the same as in Example 1, except B contributes nondepreciable property with a FMV of $100, an adjusted tax basis of $30, and subject to a liability of $20. B’s initial tax basis capital account is $10 ($30 adjusted tax basis of property contributed, less the $20 liability to which the property was subject).
Example 3: The facts are the same as in Example 1, except in Year 1, the partnership earns $100 of taxable income and $50 of tax-exempt income. A and B are each allocated $50 of the taxable income and $25 of the tax-exempt income by the partnership. At the end of Year 1, A’s tax basis capital account is increased by $75, to $175, and B’s tax basis capital account is increased by $75, to $105.
Example 4: The facts are the same as in Example 3. Additionally, in Year 2, the partnership has $30 of taxable loss and $20 of expenditures which are not deductible in computing partnership taxable income and which are not capital expenditures. A and B are each allocated $15 of the taxable loss and $10 of the expenditures which are not deductible in computing partnership taxable income and which are not capital expenditures. At the end of Year 2, A’s tax basis capital account is decreased by $25, to $150, and B’s tax basis capital account is decreased by $25, to $80. . . .
Example 5: On January 1, 2019, A and B each contribute $100 in cash to a newly formed partnership. On the same day, the partnership borrows $800 and purchases Asset X, qualified property for purposes of § 168(k), for $1,000. Assume that the partnership properly allocates the $800 liability equally to A and B under § 752. Immediately after the partnership acquires Asset X, both A and B have tax basis capital accounts of $100 and outside bases of $500 ($100 cash contributed, plus $400 share of partnership liabilities under § 752). In 2019, the partnership recognizes $1,000 of tax depreciation under § 168(k) with respect to Asset X; the partnership allocates $500 of the tax depreciation to A and $500 of the tax depreciation to B. On December 31, 2019, A and B both have tax basis capital accounts of negative $400 ($100 cash contributed, less $500 share of tax depreciation) and outside bases of zero ($100 cash contributed, plus $400 share of partnership liabilities under § 752, and less $500 of share tax depreciation).

Tax Basis Capital Account of a Partner Who Acquires the Partnership Interest from Another Partner. A partner who acquires a partnership interest from another partner, such as by purchase or in a nonrecognition transaction, has a tax basis capital account immediately after the transfer equal to the transferring partner’s tax basis capital account immediately before the transfer with respect to the portion of the interest transferred. However, any section 743(b) basis adjustment the transferring partner may have is not transferred to the acquiring partner. Instead, if the partnership has a section 754 election in effect, the tax basis capital account of the acquiring partner is increased or decreased by the positive or negative adjustment to the tax basis of partnership property under section 743(b) as a result of the transfer.

Safe-Harbor Method for Determining a Partner’s Tax Basis Capital Account. The FAQs provide a safe-harbor method for determining a partner’s tax basis capital account. Under this method,

[p]artnerships may calculate a partner’s tax basis capital account by subtracting the partner’s share of partnership liabilities under § 752 from the partner’s outside basis (safe harbor approach). If a partnership elects to use the safe-harbor approach, the partnership must report the negative tax basis capital account information as equal to the excess, if any, of the partner’s share of partnership liabilities under § 752 over the partner’s outside basis.

Certain partnerships are exempt from reporting negative tax basis capital accounts. Partnerships that satisfy four conditions (those provided in question 4 on Schedule B to Form 1065) do not have to comply with the requirement to report negative tax basis capital account information. This is because a partnership that satisfies these conditions is not required to complete item L on Schedule K-1. The four conditions are:

(a) the partnership’s total receipts for the tax year were less than $250,000;

(b) the partnership’s total assets at the end of the tax year were less than $1 million;

(c) Schedules K-1 are filed with the return and furnished to the partners on or before the due date (including extensions) for the partnership return; and

(d) the partnership is not filing and is not required to file Schedule M-3.

b. The Service has issued a draft of revised Form 1065 and Schedule K-1 for 2019. The Service has also released draft instructions for the 2019 Form 1065 and draft instructions for the 2019 Schedule K-1. Compared to the 2018 versions, the 2019 versions reflect several significant changes that likely will require a substantial amount of time in many cases on the part of those preparing the return to ensure compliance. Among the significant changes are the following:

· Reporting of tax basis capital accounts for each partner on Schedule K-1. Previous versions of Schedule K-1 gave partnerships the option to report a partner’s capital accounts on a tax basis, in accordance with GAAP, as section 704(b) book capital accounts, or on some “other” basis. Tax basis capital accounts were required beginning in 2018 only if a partner’s tax capital account at the beginning or end of the year was negative. The 2019 draft Schedule K-1 requires partnerships to report each partner’s capital account on a tax basis regardless of whether the account is negative. For partnerships that have not historically reported tax basis capital accounts, this requirement would appear to involve recalculating tax capital accounts in prior years and rolling them forward.

· Reporting a partner’s share of net unrecognized section 704(c) gain or loss on Schedule K-1. Previous versions of Schedule K-1 required reporting whether a partner had contributed property with a built-in gain or built-in loss in the year of contribution. The 2019 draft Schedule K-1 still requires partnerships to report whether a partner contributed property with a built-in gain or loss, but adds new item N in Part II, which requires reporting the “Partner’s Share of Net Unrecognized Section 704(c) Gain or (Loss).” This means that a partnership must report on an annual basis any unrecognized gain or loss that would be allocated to the partner under section 704(c) (if the partnership were to sell its assets) as a result of either the partner contributing property with a fair market value that differs from its adjusted basis or the revaluation of partnership property (such as a revaluation occurring upon the admission of a new partner).

· Separation of guaranteed payments for capital and services. Previous versions of Schedule K-1 required reporting a single category of guaranteed payments to a partner. The 2019 draft Schedule K-1 refines this category in item 4 of Part III and requires separate reporting of guaranteed payments for services, guaranteed payments for capital, and the total of these two categories.

· Reporting on Schedule K-1 more than one activity for purposes of the at-risk and passive activity loss rules. Items 21 and 22 have been added to Part III of Schedule K-1 to require the partnership to check a box if the partnership has more than one activity for purposes of the at-risk or passive activity loss rules. The 2019 draft instructions for Form 1065 indicate that the partnership also must provide an attached statement for each activity with detailed information for each activity to allow the partner to apply correctly the at-risk and passive activity loss rules.

· Section 199A deduction moved to supplemental statement. The 2018 version of Schedule K-1 required reporting information relevant to the partner’s section 199A deduction in item 20 of Part III with specific codes. The draft 2019 instructions for Form 1065 provide that, for partners receiving information relevant to their section 199A deduction, only code Z should be used in box 20 along with an asterisk and STMT to indicate that the information appears on an attached statement. According to the instructions, among other items, the statement must include the partner’s distributive share of (1) qualified items of income, gain, deduction, and loss, (2) W-2 wages, (3) unadjusted basis immediately after acquisition of qualified property, (4) qualified publicly traded partnership items, and (5) section 199A dividends (qualified REIT dividends). The statement also must report whether any of the partnership’s trades or businesses are specified service trades or businesses and identify any trades or businesses that are aggregated.

· Disregarded entity as a new category of partner on Schedule K-1. Previous versions of Schedule K-1 required the partnership to indicate whether the partner was domestic or foreign. The 2019 draft Schedule K-1 adds a new category in item H of Part II in which the partnership must indicate whether the partner is a disregarded entity and, if so, the partner’s taxpayer identification number and type of entity.

c. The Service has postponed the requirements to use tax basis capital accounts for Schedule K-1 and to report detailed information for purposes of the at-risk rules and has clarified certain other reporting requirements. In response to comments expressing concern that those required to file Form 1065 and Schedule K-1 might be unable to comply in a timely manner with the requirement to report capital accounts on a tax basis for 2019, the Treasury Department and the Service have deferred this requirement, which will now apply to partnership tax years beginning on and after January 1, 2020. According to Notice 2019-66:

This means that partnerships and other persons may continue to report partner capital accounts on Forms 1065, Schedule K-1, Item L, or 8865, Schedule K-1, Item F, using any method available in 2018 (tax basis, Section 704(b), GAAP, or any other method) for 2019. These partnerships and other persons must include a statement identifying the method upon which a partner’s capital account is reported.

The requirement to report capital accounts for 2019 using any method available in 2018 includes the requirement that partnerships that do not report tax basis capital accounts to partners must report, on line 20 of Schedule K-1 (Form 1065) using code AH, the amount of a partner’s tax basis capital both at the beginning of the year and at the end of the year if either amount is negative.

The draft 2019 Schedule K-1 included Items 21 and 22 in Part III to require the partnership to check a box if the partnership has more than one activity for purposes of the at-risk or passive activity loss rules. The 2019 draft instructions for Form 1065 also required a partnership to provide an attached statement for each activity with detailed information for each activity to allow the partner to apply correctly the at-risk and passive activity loss rules. In response to comments expressing concern that those required to file Form 1065 and Schedule K-1 might be unable to comply in a timely manner with the requirement to provide this detailed information in an attached statement, Notice 2019-66 defers this requirement. This requirement now will apply to partnership tax years beginning on and after January 1, 2020. The Notice leaves in place for 2019 the requirement that a box be checked in Items 21 and 22 in Part III of Schedule K-1 if the partnership has more than one activity for purposes of the at-risk or passive activity loss rules.

Notice 2019-66 leaves in place for 2019 the requirement that a partnership must report on an annual basis a partner’s share of “net unrecognized Section 704(c) gain or loss.” The draft 2019 instructions for Schedule K-1, however, had not defined the term “net unrecognized Section 704(c) gain or loss.” The Notice defines this term as “the partner’s share of the net (net means aggregate or sum) of all unrecognized gains or losses under section 704(c) of the Code (Section 704(c)) in partnership property, including Section 704(c) gains and losses arising from revaluations of partnership property.” This definition applies solely for purposes of completing 2019 forms. The Notice clarifies that publicly traded partnerships need not report net unrecognized section 704(c) gain for 2019 and future years until further notice. The Notice also indicates that commenters had requested additional guidance on section 704(c) computations, especially on issues such as those addressed in Notice 2009-70, which solicited comments on the rules relating to the creation and maintenance of multiple layers of forward and reverse section 704(c) gain and loss to partnerships and tiered partnerships. Notice 2019-66 provides that, “[f]or purposes of reporting for 2019, partnerships and other persons should generally resolve these issues in a reasonable manner, consistent with prior years’ practice for purposes of applying Section 704(c) to partners.”

The Notice provides that taxpayers who follow the provisions of the Notice will not be subject to any penalty for reporting in accordance with the guidance it provides.

VIII. Tax Shelters

A. Tax Shelter Cases and Rulings

There were no significant developments regarding this topic during 2019.

B. Identified “Tax-Avoidance Transactions”

There were no significant developments regarding this topic during 2019.

C. Disclosure and Settlement

There were no significant developments regarding this topic during 2019.

D. Tax Shelter Penalties

There were no significant developments regarding this topic during 2019.

IX. Exempt Organizations and Charitable Giving

A. Exempt Organizations

1. Oh goody! Changes to the UBTI rules!

Sections 13702 and 13703 of the TCJA made certain changes to the determination of unrelated business taxable income (UBTI) with respect to tax-exempt organizations. Most tax-exempt organizations are subject to federal income tax at regular rates (corporate rates for exempt corporations and trust rates for exempt trusts) on net income (i.e., after permissible deductions) from a trade or business, regularly carried on, that is unrelated to the organization’s exempt purpose (other than its need for revenue). Exceptions exist for most types of passive, investment income as well as for narrow categories of other types of income (e.g., thrift store sales). The rationale behind the changes to the UBTI rules was to put tax-exempt organizations on par with taxable organizations with respect to certain types of compensation and fringe benefits. Because, however, disallowing deductions for fringe benefits such as parking and transportation expenses (which is what section 13304(c) of the TCJA did by adding section 274(a)(4)) does not work for exempt organizations, which do not normally pay tax, Congress did something weird. Specifically, Congress decided to arbitrarily increase an exempt organization’s unrelated business income (even if such income was otherwise zero) by the value of the fringe benefits the organization provides to employees. Sounds like a simple solution, right? Wrong! See below.

Stop using good UBI money to chase bad UBI money! Under pre-TCJA law, if an exempt organization had unrelated business income (UBI) from one activity, but unrelated losses from another activity, then the income and losses could offset, meaning that the organization would report zero or even negative UBI. Congress apparently didn’t like this result, so under new section 512(a)(6) income and losses from separate unrelated businesses may no longer be aggregated. This new UBI provision is effective for taxable years beginning after 2017, thus giving fiscal-year nonprofits some time to plan. Moreover, under a special transition rule, UBI net operating losses arising in a taxable year beginning before January 1, 2018, that are carried forward to a taxable year beginning on or after such date, are not subject to section 512(a)(6).

Congress doesn’t like using UBI to help fund fringe benefits, so when your organization’s highly compensated employees are pumping iron at the charity’s free gym, you can pump up your UBI too. Under new section 512(a)(7), an organization’s UBTI is increased by the amount of any expenses paid or incurred by the organization that are not deductible because of the limitations of section 274 for (1) qualified transportation fringe benefits (as defined in section 132(f)), (2) a parking facility used in connection with qualified parking (as defined in section 132(f)(5)(C)), or (3) any on-premises athletic facility (as defined in section 132(j)(4)(B)). New section 512(a)(7) is effective for amounts paid or incurred after 2017, so affected tax-exempt organizations need to deal with this change immediately. The Service has granted some relief, though, under Notice 2018-100, discussed further below. Moreover, Notice 2018-100 clarifies that with respect to on-premises athletic facilities UBI is increased under section 512(a)(7) only if the benefits provided discriminate in favor of highly compensated employees.

Perhaps worth noting here. Because the TCJA reduced the top federal income tax rate on C corporations to 21%, it likewise reduced to 21% the top rate on UBI of tax-exempt organizations formed as nonprofit corporations, which are the vast majority. So, the news for tax-exempts is not all bad.

a. A tax law oxymoron: nonprofit trades or businesses. Huh? Organizations described in sections 401(a) (pension and retirement plans) and 501(c) (charitable and certain other entities) generally are exempt from federal income taxation. Nevertheless, sections 511 through 514 impose federal income tax upon the UBTI of such organizations, including for this purpose state colleges and universities. The principal sources of UBTI are sections 512 and 513 “unrelated trade or business” gross income (minus deductions properly attributable thereto) and section 514 “unrelated debt-financed income” (minus deductions), including a partner’s allocable share of income from a partnership generating UBTI.

Prior to the TCJA, exempt organizations could aggregate income and losses from unrelated trades or businesses before determining annual UBTI potentially subject to tax. Excess losses (if any) after aggregating all UBTI-related items of an exempt organization created a net operating loss subject to the rules of section 172. Effective for taxable years beginning after 2017, however, TCJA added new section 512(a)(6) to disaggregate unrelated trades or businesses of exempt organizations for purposes of determining UBTI. Specifically, new section 512(a)(6) provides that for any exempt organization with more than one unrelated trade or business: (1) UBTI must be computed separately (including for purposes of determining any net operating loss deduction) for each such unrelated “trade or business” and (2) total annual UBTI is equal to (i) the sum of positive UBTI from each such separate “trade or business” minus (ii) the specific $1,000 deduction allowed by section 512(b)(12). Under a special transition rule, UBI net operating losses arising in a taxable year beginning before January 1, 2018 and carried forward to a taxable year beginning on or after such date are not subject to new section 512(a)(6).

Now we get to the crux of the matter. The logical result of new section 512(a)(6) is that every exempt organization must segregate its unrelated trade or business income and losses for purposes of determining its annual UBTI. Yet, the Treasury Department and the Service have never defined separate “trades or businesses” for this purpose or, frankly, for any other federal income tax purpose. Further complicating matters, TCJA also enacted a related subsection, new section 512(a)(7), that increases an exempt organization’s UBTI by expenses for which a deduction is disallowed under certain provisions of sections 274 and 132 (specified transportation, parking, and athletic facility fringe benefits) unless the expense is “directly connected with an unrelated trade or business which is regularly carried on by the organization.” Thus, new section 512(a)(7) also requires identification of each unrelated “trade or business” of an exempt organization, but section 512(a)(7) has the further deleterious effect of potentially creating UBTI for an exempt organization that otherwise has no unrelated trade or business. In Notice 2018-67, the Treasury Department and Service took the first step toward providing guidance with respect to both sections 512(a)(6) and (7) and delineating separate trades or businesses for UBTI purposes.

What’s in the Notice? Aside from requesting comments, Notice 2018-67 is lengthy (36 pages) and contains 13 different “sections,” ten of which address substantive, technical aspects of new sections 512(a)(6) and (7). The high points are summarized below, but Notice 2018-67 is a must-read for tax advisers to section 501(c) organizations, state colleges and universities, and section 401(a) pension and retirement plans, especially when those entities have UBTI from partnership interests they hold as investments. To summarize:

(i) General Rule. Until proposed regulations are published, all exempt organizations affected by the changes to sections 512(a)(6) and (7) may rely upon a “reasonable, good-faith interpretation” of sections 511 through 514, considering all relevant facts and circumstances, for purposes of determining whether the organization has more than one unrelated trade or business. Because of the way section 512(a)(6) operates, exempt organizations will be inclined to conclude that they have only one unrelated trade or business, but that is not easy to do given the so-called “fragmentation” principle of section 513(c) and Regulation section 1.513-1(b). For example, advertising income earned by an exempt organization (e.g., National Geographic) from ads placed in the organization’s periodical is UBTI even if subscription income is not UBTI. For an exempt organization this general rule includes using a reasonable, good-faith interpretation when determining: (1) “[w]hether to separate debt-financed income described in sections 512(b)(4) and 514”; (2) “[w]hether to separate income from a controlled entity described in section 512(b)(13)”; and (3) “[w]hether to separate insurance income earned through a controlled foreign corporation as described in section 512(b)(17).” The use of the 6-digit code North American Industry Classification System for segregating trades or businesses will be considered a reasonable, good-faith interpretation until regulations are proposed.

(ii) Partnership Interests. In general, partnership activities are attributable to partners such that holding a partnership interest can result in multiple lines of UBTI being considered allocable to an exempt organization partner. Until proposed regulations are issued, however, exempt organizations (other than section 501(c)(7) social clubs) may rely upon either of two rules for aggregating multiple lines of UBTI from a partnership, including UBTI attributable to lower-tier partnerships and unrelated debt-financed income:

The “interim rule” permits the aggregation of multiple lines of UBTI from an exempt organization’s interest in a single partnership if the partnership meets either a “de minimis test” or a “control test.” The de minimis test generally is met if the exempt organization partner holds a two-percent-or-less capital and profits interest in a partnership. The control test generally is met if the exempt organization partner holds a 20%-or-less capital interest in a partnership and does not have “control or influence” over the partnership. Control or influence over a partnership is determined based upon all relevant facts and circumstances. For purposes of determining an exempt organization’s percentage interest in a partnership under the interim rule, partnership interests held by disqualified persons (as defined in section 4958), supporting organizations (as defined in section 509(a)(3)), and controlled entities (as defined in section 512(b)(13)(D)) must be considered.

The “transition rule” permits the aggregation of multiple lines of UBTI from an exempt organization’s interest in a single partnership if the interest was acquired prior to August 21, 2018. “For example, if an organization has a thirty-five percent interest in a partnership [acquired] prior to August 21, 2018, it can treat the partnership as being in a single unrelated trade or business even if the partnership’s investments generated UBTI from various lower-tier partnerships that were engaged in multiple types of trades or businesses . . .” (or, presumably, from debt-financed income).

(iii) IRC section 512(a)(7). Income under section 512(a)(7) (i.e., the UBTI increase for expenses not directly connected with an unrelated trade or business regularly carried on by the organization and for which a deduction is disallowed under certain provisions of sections 274 and 132 (specified transportation, parking, and athletic facility fringe benefits)) is not income from a trade or business for purposes of section 512(a)(6). Thus, such UBTI appears to be entirely separate from section 512(a)(6) income and therefore not offset by any deductions or losses.

(iv) GILTI. An exempt organization’s inclusion of global intangible low-taxed income (GILTI) under section 951A is treated as a dividend which is not UBTI (pursuant to section 512(b)(1)) unless it is debt-financed (and thus included in UBTI under section 512(b)(4)).

b. Guidance on determining the increase to UBTI for employer-provided parking. In Notice 2018-99, the Service announced that the Treasury Department and the Service will issue proposed regulations under sections 274 and 512 that will include guidance on determining the calculation of increased UBTI of tax-exempt organizations that provide qualified transportation fringes (and also the nondeductible parking expenses and other expenses for qualified transportation fringes provided by nontax-exempt employers). Until further guidance is issued, employers that own or lease parking facilities where their employees park can rely on interim guidance provided in the Notice to determine the increase in the amount of UBTI under section 512(a)(7) attributable to nondeductible parking expenses. The guidance in the Notice for determining the increase in UBTI mirrors the guidance for determining the nondeductible parking expenses of nontax-exempt employers. The Notice explains that an increase to UBTI is not required “to the extent the amount paid or incurred is directly connected with an unrelated trade or business that is regularly carried on by the organization” because, in such a case, the expenses for qualified transportation fringes are disallowed by section 274(a)(4) as a deduction in calculating the UBTI of the unrelated trade or business. The Notice confirms that the effect of the increase in UBTI can be to require a tax-exempt organization to file Form 990-T, Exempt Organization Business Income Tax Return, if the organization’s gross income included in computing UBTI is $1,000 or more. The rules for determining the increase in UBTI are illustrated by Examples 9 and 10 in the Notice.

c. Never had UBTI or paid estimated taxes thereon? Not to worry, says the Service. Prior to the enactment of section 512(a)(7), many if not most section 501(c)(3) organizations had never reported UBTI or paid any unrelated business income tax (UBIT) thereon. Organizations that owe UBIT are required to pay estimated taxes or suffer penalties. Furthermore, because these organizations have never paid UBIT, they would not be eligible for the safe-harbor exclusion for estimated taxes under section 6655(d)(1) (estimated payments equal to prior year’s UBIT). Accordingly, with new section 512(a)(7) catching most tax-exempt organizations off guard, the Service issued Notice 2018-100 and decided “in the interest of sound tax administration” (in other words, to prevent another Boston Tea Party) to waive the penalty for failure to make estimated UBIT payments for such exempt organizations. The penalty waiver is limited, however, to

tax-exempt organizations that provide qualified transportation fringes (as defined in section 132(f)) and any parking facility used in connection with qualified parking (as defined in section 132(f)(5)(C)) to an employee to the extent that the underpayment of estimated income tax results from enactment of section 13304(c) and section 13703 of the [TCJA].

Furthermore, the relief is available only to tax-exempt organizations that were not required to file a Form 990-T (the UBIT form) for the taxable year immediately preceding the organizations’ first taxable year ending after December 31, 2017. Notice 2018-100 does not address the possibility of estimated UBIT payments attributable to discriminatory on-premises athletic facilities. To avail themselves of the relief granted by the Notice, exempt organizations must write “Notice 2018-100” on the top of the organization’s Form 990-T.

d. Much Ado About Nothing. Congress has repealed with retroactive effect the increase to UBTI for nondeductible fringe benefits provided by tax-exempt organizations. Section 302 of the Taxpayer Certainty and Disaster Tax Relief Act of 2019 repealed section 512(a)(7). Under former section 512(a)(7), a tax-exempt organization’s UBTI was increased by the amount of any expenses paid or incurred by the organization that were not deductible because of the limitations of section 274 for (1) qualified transportation fringe benefits (as defined in section 132(f)), (2) a parking facility used in connection with qualified parking (as defined in section 132(f)(5)(C)), or (3) any on-premises athletic facility (as defined in section 132(j)(4)(B)). The repeal is effective retroactively as if the repeal had been part of the TCJA. In other words, section 512(a)(7) never took effect. Tax-exempt organizations should be entitled to a refund of any UBIT paid pursuant to former section 512(a)(7).

2. Successful private colleges and universities really must be in the dog house because, in addition to taxing them for highly-paid coaches, Congress has decided to tax their endowments too! And, just to keep us on our toes, the legislative history says the statute turns on the number of an institution’s “tuition-paying” students, but section 4968 simply reads “students.”

Section 13701 of the TCJA added section 4968 which imposes a 1.4% annual excise tax on the net investment income of certain private colleges and universities and affiliated organizations with endowments worth $500,000 or more per full-time student. The excise tax imposed by section 4968 is similar in many respects to the annual excise tax imposed on private foundations under section 4940. In particular, section 4968 applies to an “applicable educational institution,” which is defined as institution that (1) is an “eligible educational institution” described in section 25A(f)(2) (which in turn refers to 20 U.S.C. section 1088), (2) has at least 500 students during the preceding taxable year more than 50% of which are in the U.S., (3) is not described in the first section of section 511(a)(2)(B) (state colleges and universities), and (4) has assets (other than assets used directly in carrying out the institution’s exempt purpose) with an aggregate fair market value as of the end of the preceding taxable year of at least $500,000 per student. For this latter purpose, the number of students of an institution is based on the daily average number of full-time students attending the institution, with part-time students taken into account on a full-time student equivalent basis. Moreover, the legislative history of section 4968 states that the $500,000 per student figure should be calculated based upon “tuition-paying” students; however, the Senate Parliamentarian struck that language from section 4968 immediately before it was passed by the House and Senate. Whether regulations can fill in the gap is anybody’s guess. Section 4968 is permanent and effective for taxable years beginning after 2017, again giving fiscal-year private colleges and universities time to cope.

a. Maybe students negotiating for scholarships at private colleges and universities now have a little more leverage. As originally passed late in 2017, section 4968 taxed private colleges and universities (and affiliates) with endowments of $500,000 or more per “student” (as defined in the statute to account for full and part-time students); however, the legislative history of section 4968 stated that the $500,000 per student figure should be calculated based upon “tuition-paying” students. The discrepancy between the statute and the legislative history was created because the Senate Parliamentarian struck the “tuition-paying” language from section 4968 immediately before the TCJA ultimately was passed by Congress. Thanks to section 41109 of the Bipartisan Budget Act of 2018, section 4968 has been amended to include the “tuition-paying” language. Thus, only those private colleges and universities (and affiliates) with endowments of $500,000 or more per tuition-paying student will be subject to the 1.4% annual excise tax.

b. Then again . . . maybe not! In Notice 2018-55, the Service has announced that proposed regulations under section 4968 will determine “net investment income” gains and losses of an “applicable educational institution” by reference to an endowment asset’s fair market value as of December 31, 2017, not its historical adjusted basis (unless historical adjusted basis is greater than fair market value as of December 31, 2017). This special rule allowing an applicable educational institution to use the greater of (1) fair market value as of the end of the taxable year of enactment of the statute or (2) historical adjusted basis for purposes of calculating net investment income is patterned after the approach taken in 1969 with respect to private foundations subject to section 4940. Therefore, net investment income of applicable educational institutions subject to section 4968 should be minimal for the next year or so. Notice 2018-55 further announces that proposed regulations under section 4968 will (1) take into account net investment losses only to the extent of net investment gains (with no allowance for capital loss carryovers or carrybacks) and (2) permit related organizations described in section 4968(d)(2) to consolidate gains and losses for purposes of calculating net investment income. Notice 2018-55 also invites comments by September 6, 2018, regarding the to-be-proposed regulations under section 4968.

c. Proposed Regulations issued under section 4968. The Service received only two written comments in response to Notice 2018-55, resulting in the release of Proposed Regulations that largely follow the guidance announced in the Notice; however, the Proposed Regulations expound upon certain key terms used in section 4968, including “applicable educational institution,” “tuition-paying students,” “assets used directly in carrying out an institution’s exempt purpose,” and “related organizations.” The Proposed Regulations will apply to tax years beginning after the date that final regulations are published; however, taxpayers may rely on the Proposed Regulations for tax years beginning before publication of final regulations.

Interesting factoid. According to the Service, roughly 40 or fewer institutions are affected by section 4968.

3. Has so-called “dark money” become virtually invisible (except to the Service, of course)?

Oversimplifying a bit for the sake of convenience, since 1969 section 6033(b)(5) has required section 501(c)(3) organizations to disclose on their annual information returns (Form 990) certain contributions as well as “the names and addresses of [the organization’s] substantial contributors” for the year. Section 507(d)(2) defines a “substantial contributor” as any person contributing $5,000 or more to an organization if such amount is greater than two percent of the total contributions to the organization during the taxable year. Regulation section 1.6033-2 extended this disclosure requirement to other types of organizations exempt under section 501(a), including section 501(c)(4) “social welfare” organizations and section 501(c)(6) “trade associations.” In particular, some section 501(c)(4) social welfare organizations have been created and funded to engage in lobbying and political campaign activity that is prohibited to section 501(c)(3) organizations. This use of section 501(c)(4) organizations has been termed “dark money” by some and is controversial. Although the names and addresses of “dark money” contributors were supposed to be redacted on the organization’s Form 990 made publicly available by the Service pursuant to section 6104(b), some inadvertent disclosures have occurred. Reportedly, a few of the largest organizations impacted have been entities affiliated with the National Rifle Association, the U.S. Chamber of Commerce, and Americans for Prosperity, the latter being tied to billionaires Charles and David Koch.

Under Revenue Procedure 2018-38, the Service determined that the disclosure of the names and addresses of substantial contributors would no longer be required on a non-501(c)(3) organization’s annual Form 990. As stated in the Revenue Procedure,

[t]he IRS does not need personally identifiable information of [such] donors to be reported . . . in order for it to carry out its responsibilities. The requirement to report such information increases compliance costs for some private parties, consumes IRS resources in connection with the redaction of such information, and poses a risk of inadvertent disclosure of information that is not open to public inspection.

The reporting changes announced by Revenue Procedure 2018-38 are effective for taxable years ending on or after December 31, 2018. Notwithstanding this relief from disclosure granted to section 501(a) organizations other than 501(c)(3)s, Revenue Procedure 2018-38 states that the affected organizations must maintain donor information in the organization’s books and records in case such information is requested by the Service.

a. ♫♪ This little light of mine, I’m gonna let it shine . . .” ♪♫. In a suit brought by Governor Stephen Bullock (also a former Democratic candidate for President in 2020), the District Court for the District of Montana (Judge Morris) set aside Revenue Procedure 2018-38 for failure to comply with the Administrative Procedure Act (APA). Governor Bullock had argued that, although the Commissioner has discretion to determine whether the names and addresses of substantial contributors must be disclosed on annual information returns filed by exempt organizations other than 501(c)(3)s, the change announced in Revenue Ruling 2018-38 was a new “legislative rule.” As such, the Treasury Department and the Service had to comply with the notice-and-comment procedures of the APA (which they did not do) before issuing Revenue Procedure 2018-38. The Treasury Department and the Service maintained that, because Revenue Procedure 2018-38 was merely a “procedural rule” and not a “legislative rule,” the APA’s notice-and-comment requirements did not apply. Judge Morris disagreed and sided with Governor Bullock to hold that the Treasury Department and the Service should have complied with the APA before issuing Revenue Procedure 2018-38.

b. OK, you win for now. We’ll go over to the “darkside” soon. Apparently believing that Governor Bullock had a valid point, the Treasury Department and the Service have issued Proposed Regulations under section 6033 that ultimately will implement the guidance set forth in Revenue Procedure 2018-38. The Proposed Regulations generally provide that only section 501(c)(3) organizations must disclose the names and addresses of substantial contributors on their annual Form 990 information returns. Although section 501(c)(4) and certain other non-501(c)(3) exempt organizations will no longer be required to disclose names and addresses of substantial contributors on their annual information returns once the Proposed Regulations become final, such organizations nevertheless are required to keep records (which can be requested by the Service) containing such information.

Note. Section 527 political organizations must continue to report the names and addresses of substantial contributors.

4. The 11-factor facts-and-circumstances test for political campaign activity by tax-exempts set forth in Revenue Ruling 2004-6 is neither unconstitutionally vague nor overbroad, at least on its face.

In Freedom Path, Inc. v. Internal Revenue Service, an unreported decision from the District Court for the Northern District of Texas, Judge Fitzwater upheld Revenue Ruling 2004-6, as being neither unconstitutionally vague nor overbroad on its face for purposes of determining impermissible political campaign activity by a section 501(c)(4) organization. Revenue Ruling 2004-6 sets forth an 11-factor facts-and-circumstances test used by the Service to determine whether certain activity by tax-exempt section 501(c)(3) or (c)(4) organizations is impermissible political campaign activity. The Service preliminarily denied exempt section 501(c)(4) status to Freedom Path, Inc. on the basis that its proposed activities were primarily political in nature. Freedom Path then sued former Exempt Organizations Director Lois Lerner and the Service before the Service even issued a final negative determination letter to Freedom Path.

The opinion in this case is the fourth ruling issued by Judge Fitzwater in a series of claims made in this ongoing lawsuit against the Service and Lerner alleging that conservative section 501(c)(4) groups had been targeted for denial of tax-exempt status during the 2011–2012 election cycle. The specific issue in this case was whether Revenue Ruling 2004-6 was unconstitutional on its face under either the First Amendment (free speech) or Fifth Amendment (due process) for being vague or overbroad. Judge Fitzwater held that it was not. The next and fifth ruling in this case almost certainly will be whether the 11-factor test in Revenue Ruling 2004-6 was applied in an unconstitutional manner by the Service to preliminarily deny section 501(c)(4) exempt status to Freedom Path, Inc. Stay tuned . . . .

a. Meanwhile, prompted by the Service, the Fifth Circuit had another idea how to resolve the issue of the facial challenge to Revenue Ruling 2004-6. On appeal of the narrow issue regarding whether Revenue Ruling 2004-6 is unconstitutional on its face, the Court of Appeals for the Fifth Circuit, in an opinion written by Judge Southwick, decided Freedom Path lacked standing to sue. Freedom Path had made the same arguments before the Fifth Circuit as it had made before Judge Fitzwater. Cleverly, though, the Service argued before the Fifth Circuit that Revenue Ruling 2004-6 technically was not applied to deny Freedom Path’s application for exempt status under section 501(c)(4). (The Service had not made this argument before Judge Fitzwater.) Rather, the Service pointed out that the facts-and-circumstances test described in Revenue Ruling 2004-6 was considered by the Service, along with other authorities, as part of the decision to deny 501(c)(4) status to Freedom Path, but the actual application of Revenue Ruling 2004-6 by its terms relates to determining an exempt organization’s tax liability (if any) under section 527 (political organizations). Furthermore, argued the Service, Freedom Path has no tax liability under section 527. Thus, the Service concluded, Revenue Ruling 2004-6 is not the source of the alleged injury to Freedom Path.

The Fifth Circuit agreed with the Service’s analysis and determined that Freedom Path did not have standing because its claim (i.e., denial of 501(c)(4) status) was not “fairly traceable” to the text of Revenue Ruling 2004-6. Therefore, the Fifth Circuit vacated Judge Fitzwater’s opinion (which had considered but rejected Freedom Path’s constitutional challenge to Revenue Ruling 2004-6) and remanded the case to be dismissed for lack of jurisdiction. As noted above, Freedom Path’s claim that it was unconstitutionally denied 501(c)(4) status (as opposed to its claim that Revenue Ruling 2004-6 is unconstitutional on its face) remains subject to challenge by Freedom Path and likely will be the next chapter in this story.

5. Provisions of the Taxpayer First Act affecting tax-exempt organizations.

a. Mandatory e-filing by tax-exempt organizations. Section 3101 of the Taxpayer First Act amends section 6033 by redesignating subsection (n) as subsection (o) and adding new subsection (n). New section 6033(n) requires all organizations that are exempt from tax under section 501(a) and that are required by section 6033 to file returns to do so electronically. The legislation also amends section 527(j)(7) to require e-filing of all reports required by section 527(j)(2) and amends section 6011 by adding new section 6011(h), which requires e-filing of all UBIT returns. The legislation also amends section 6104(b) to require the Service to make available in machine readable format as soon as practicable all annual returns e-filed under section 6033(n).

Generally, all of these amendments apply to taxable years beginning after July 1, 2019 (the date of enactment). Transitional relief is provided for certain organizations. First, for certain small organizations or other organizations for which the Secretary of the Treasury determines that application of the e-filing requirement would “cause undue burden without a delay,” the Secretary of the Treasury has discretion to delay the application of the requirement to file electronically provided that the delay does not apply to any taxable year later than the taxable year beginning two years following July 1, 2019 (the date of enactment). Second, the Secretary of the Treasury has discretion to delay the effective date not later than taxable years beginning two years after the date of enactment for the filing of Form 990-T (reports of UBTI or the payment of a proxy tax under section 6033(e) by certain tax-exempt organizations that incur nondeductible lobbying and political expenses).

b. The Service must provide notice to tax-exempt organizations before revocation of tax-exempt status for failure to file required returns. Under section 6033(j)(1), if an organization fails to file a required Form 990-series return or notice for three consecutive years, the organization’s tax-exempt status is automatically revoked. Section 3102 of the Taxpayer First Act amends section 6033(j)(1) to require the Service to notify a tax-exempt organization that fails to file a required return or notice for two consecutive years that the Service has no record of having received such returns or notices and that the organization’s tax-exempt status will be revoked if the organization fails to file the next required return or notice by the applicable due date. The notification must contain information about how to comply with the annual information return and notice requirements under sections 6033(a)(1) and 6033(i). This requirement applies to failures to file returns or notices for two consecutive years if the return or notice for the second year is required to be filed after December 31, 2019.

B. Charitable Giving

1. It took some time, but finally we “gotcha,” says the Service, in this infamous charitable contribution case involving billionaire and Miami Dolphins’ owner Stephen Ross and the University of Michigan.

In RERI Holdings I, LLC v. Commissioner, a TEFRA case that has gone on for some time and has produced at least one other noteworthy holding (see below), the Service prevailed in denying a $33 million charitable contribution deduction to a partnership in which Stephen Ross, owner of the Miami Dolphins, was a partner. The property was donated to the University of Michigan, Ross’s alma mater. The partnership had paid only $2.95 million for the property a little over a year prior to its donation. In fact, at some point after the donation, the University of Michigan sold the property for only $1.94 million. These facts, of course, displeased the Service greatly, and the Service convinced the Tax Court to deny the partnership’s charitable contribution deduction on technical grounds (as discussed below). Moreover, contrary to decisions of the Fifth and Ninth Circuits in Heasley v. Commissioner and Gainer v. Commissioner, the Tax Court (Judge Halpern) determined that the partners of the partnership are potentially liable for aggregate gross valuation misstatement penalties of about $11.8 million.

The facts of the case are complicated but essentially reveal that, for tax year 2003, the partnership claimed a $33 million charitable contribution deduction under section 170(a)(1) for a donation to the University of Michigan. The donated property consisted of a remainder interest in a disregarded single-member LLC that the partnership owned and that held underlying real property. On its Form 8283, Noncash Charitable Contributions, the partnership failed to report its “cost or adjusted basis” for the donated property as required by Regulation section 1.170A-13(c)(4)(ii)(E), instead leaving the line on the form completely blank. Judge Halpern ruled that this failure to comply either strictly or substantially with the Regulations was fatal to a claimed charitable contribution deduction, thereby denying the deduction in full. Lastly, for purposes of determining potential penalties, the Tax Court held that the correct value of the property at the time of the donation was approximately $3.5 million.

Regarding the Service’s assertion of the 40% penalty under section 6662(h) for “gross valuation misstatements” (valuation of 400% or more of the correct value), the partnership argued that section 6662 should not apply because the $33 million charitable contribution deduction was completely disallowed and hence was not “attributable to” a valuation misstatement. Judge Halpern’s opinion, however, relies on the Tax Court’s decision in AHG Investments, LLC v. Commissioner, in which the court concluded that “a taxpayer may not avoid the gross valuation misstatement penalty merely by conceding a deduction or credit on a ground unrelated to value or basis of property” and declined to follow the decisions in Heasley and Gainer by the Fifth and Ninth Circuits holding to the contrary. Because any appeal by the partnership (due to its dissolution in 2004) would be to the Court of Appeals for the D.C. Circuit, the Tax Court was free to follow its decision in AHG Investments, LLC. Judge Halpern then determined that the correct fair market value of the donated property should have been roughly $3.5 million, i.e., $29.5 million less than the value claimed by the partnership. Therefore, subject to partner-level section 6662(e)(2) calculations ($5,000 underpayment threshold per partner), the partners of the partnership potentially are liable for penalties aggregating as much as $11.8 million (40% of the $29.5 million valuation overstatement).

The Service probably thought it should have won this case previously on a similar technicality. In RERI Holdings I, LLC v. Commissioner, the Service had cleverly argued on a summary judgment motion that the partnership’s “qualified appraisal” of the property was fatally flawed. Specifically, the Service had argued that although the partnership obtained an otherwise qualified appraisal, the partnership’s appraisal valued a remainder interest in the underlying real property, not the remainder interest in the disregarded single-member LLC that held the real property. The remainder interest in the disregarded single-member LLC was the property the partnership donated to the University of Michigan, not the real property itself. Thus, argued the Service, the partnership’s otherwise qualified appraisal was for the wrong property (even though under section 7701 the single-member LLC was completely disregarded for all other tax purposes)! But, in 2014 Judge Halpern did not let the Service win so easily. Judge Halpern accepted the Service’s argument that a charitable contribution of an interest in a disregarded single-member LLC should be viewed differently (and perhaps valued differently) than a charitable contribution of the underlying asset(s). Judge Halpern so held even while acknowledging that a single-member LLC otherwise is ignored for federal tax purposes. Judge Halpern’s opinion relied heavily on the Tax Court’s earlier decision in a gift tax case involving a disregarded single-member LLC. Nevertheless, perhaps to avoid so easily granting summary judgment against the taxpayer and in favor of the Service, Judge Halpern reasoned that there was an unresolved issue of material fact whether a valuation of the real property held by the partnership’s disregarded single-member LLC could “stand proxy” for the otherwise required “qualified appraisal.” Surprisingly, though, Judge Halpern’s decision in the earlier RERI Holding ruling raises the prospect of a disregarded single-member LLC interest being regarded and valued separately for purposes of determining charitable contributions under section 170.

a. Fumble? Touchdown Service? Game over? Pick your pun, but it might be time for this taxpayer to admit defeat. Fiddlesticks!!! In Blau v. Commissioner, the Court of Appeals for the D.C. Circuit (Judge Ginsburg) has affirmed the holding of the Tax Court that the taxpayer’s failure to report its “cost or adjusted basis” for donated property on Form 8283, Noncash Charitable Contributions, as required by Regulation section 1.170A-13(c)(4)(ii)(E), was fatal to the taxpayer’s claimed $33 million charitable contribution deduction. The court also upheld the Tax Court’s imposition of a 40% gross valuation misstatement penalty under section 6662(h) even though the claimed charitable contribution deduction ultimately was disallowed.

After summarizing the facts and procedural posture of the case, the D.C. Circuit explained that, even assuming for the sake of argument that the requirements of Regulation section 1.170A-13(c)(4)(ii)(E) can be met by substantial compliance as the taxpayer had claimed in the Tax Court and on appeal, the taxpayer had not in fact substantially complied with the Regulation because it left a blank line on the Form 8283 instead of providing any information whatsoever as to its cost or adjusted basis in the donated property. The court also rejected all four of the taxpayer’s arguments (one of which was new) and upheld the Tax Court’s imposition of the 40% gross valuation misstatement penalty under section 6662(h). With regard to this latter ruling upholding the Tax Court, the court reasoned as follows. First, the taxpayer argued de novo that the Service failed to obtain the supervisory approval required under section 6751(b) before imposing a penalty under section 6662, relying on the decision of the Second Circuit in Chai v. Commissioner. The court rejected this new argument by the taxpayer, however, because the argument had not been raised previously in the Tax Court (notwithstanding the fact that Chai had not been decided at the time the taxpayer was before the Tax Court). Responding to the taxpayer’s contention that it did not raise the argument in Tax Court because Chai had not been decided and the Tax Court’s prior position at the time was that supervisory approval was not required under section 6751(b) until assessment, the court wrote: “Fiddlesticks. The fact is that when RERI was before the Tax Court, it ‘was free to raise the same, straightforward statutory interpretation argument the taxpayer in Chai made’ there.” Second, the court agreed with the Tax Court’s rejection of the taxpayer’s “attributable to” argument, which previously had been addressed by Judge Halpern. Third, the court rejected the taxpayer’s argument that Judge Halpern failed to properly value the donated property for purposes of determining the gross valuation misstatement penalty. Finally, the court rejected the taxpayer’s argument that it had met the “reasonable cause” exception for avoiding the gross valuation misstatement penalty of section 6662(h). Judge Halpern similarly had ruled that the taxpayer did not meet the “reasonable cause” exception; however, Judge Halpern concluded that the Service had met its burden of proof under Rule 142 that reasonable cause was lacking whereas the appeals court reasoned that, regardless, the taxpayer did not show reasonable cause and did not qualify for the exception irrespective of whether the Service must show a lack of reasonable cause under Rule 142.

2. Personally evangelizing for “BSDM”—pay attention; we didn’t write “BDSM”—doesn’t allow you to take charitable contribution deductions for your unreimbursed expenses.

Although expenses incurred “for the use of” a charitable organization can be deductible under section 170, the Tax Court in Oliveri v. Commissioner held that this taxpayer took things a little too far. (Sometimes you really can’t help but wonder, “What were they thinking?” when reading certain Tax Court cases. This is one of those cases.) The taxpayer was a former U.S. Air Force pilot who upon his retirement from the Air Force became very active in the Catholic Church. The taxpayer frequently attended church-related meetings, participated in community outreach efforts, and assisted various church officials. In 1987, the taxpayer was certified as a teacher and trainer for the Catholic Church following his completion of a 16-week Catholic evangelization trainer’s program. Since that time, the taxpayer devoted his life to evangelism on behalf of the Catholic Church. The taxpayer considered all of his contact with the public an opportunity for evangelism, and he would wear a large and visible crucifix at all times. The taxpayer evangelized and discussed his faith with friends, members of his extended family, and members of the religious organization that he founded, The Brothers and Sisters of the Divine Mercy (BSDM). (No, we’re not kidding. The acronym used by the Tax Court really was “BSDM.”) The taxpayer incurred significant expenses in connection with his BSDM and Catholic Church evangelism activities in 2012, including costs for piloting and flying a leased airplane, commercial airfare, other transportation, lodging, meals, gifts for needy individuals and members of BSDM, etc. The taxpayer’s 2012 unreimbursed expenses in this regard totaled at least $39,979, all of which he deducted as charitable contributions. None of the taxpayer’s activities or expenses, however, were expressly authorized by the Catholic Church, and the Catholic Church did not provide the taxpayer with contemporaneous written acknowledgments for his expenses.

After restating the general rule of Van Dusen v. Commissioner that to be deductible under section 170 unreimbursed expenses must be subject to coordination, supervision, or oversight by a charitable organization, the Tax Court (Judge Colvin) had little trouble denying the taxpayer’s claimed deductions in this case. The Tax Court reasoned that, not only did the unreimbursed expenses fail to meet the Van Dusen standard, most of the taxpayer’s expenses were incurred in whole or in part for personal purposes. Furthermore, with respect to unreimbursed expenses of $250 or more attendant to rendering services on behalf of a charity, a taxpayer must obtain a contemporaneous written acknowledgment to comply with Regulation section 1.170A-13(f)(10). The taxpayer did not obtain such written acknowledgment, even from BSDM, the organization he founded. Perhaps, though, divine intervention did play a role in this case. The Tax Court held that the Service could not impose accuracy-related penalties against the taxpayer because prior, written supervisory approval had not been obtained as required by section 6751(b)(1).

3. ♫♪ “Workin’ in the coal mine . . . Oops, about to slip down” ♪♫ on the extinguishment clause requirement of Regulation section 1.170A-14(g)(6)(ii).

In Coal Property Holdings, LLC v. Commissioner, the Service seems to have found a silver (coal?) bullet to kill a number of the conservation easement cases in the form of Regulation section 1.170A-14(g)(6)(ii), which provides that a deduction is allowed for the donation of a conservation easement only if the donor agrees that the donee will receive a portion of any proceeds from the subsequent extinguishment of the easement at least equal to the proportionate value of the perpetual conservation restriction (sometimes referred to as the “extinguishment clause” requirement). The extinguishment clause requirement forms part of the rule set forth in section 170(h)(5)(A), which provides that a contribution shall not be treated as exclusively for conservation purposes unless the conservation purpose is protected in perpetuity. We previously have reported on a number of similar conservation easement cases decided against taxpayers. In this latest case, the Tax Court (Judge Lauber) largely followed the reasoning adopted in the prior cases to disallow the taxpayer’s claimed $155.5 million charitable contribution deduction.

Facts. The taxpayer, Coal Property Holdings, LLC, acquired 3,713 acres of property in September, 2013. The property had been used in the past for the surface mining of coal. Three weeks later an “entity owned by an investor”—we’re guessing an LLC formed to facilitate the intended conservation easement charitable deduction—acquired a 99% interest in the taxpayer for $32.5 million. Three days later, the taxpayer donated a conservation easement over the property to a Tennessee land trust. The conservation easement deed prohibited any future surface mining on the property (as required by section 170(h)(5)); however, as discussed further below, the deed reserved to the taxpayer certain other rights with respect to the property. The taxpayer subsequently claimed a $155.5 million charitable contribution deduction on its 2013 federal income tax return. Upon audit, the Service completely disallowed the taxpayer’s $155.5 million deduction.

The taxpayer timely petitioned the Tax Court, and the Service moved for partial summary judgment on the basis that the “extinguishment clause” in the conservation easement deed failed to satisfy the strict requirements of Regulation section 1.170A-14(g)(6)(ii). The “extinguishment clause” in issue (apparently one that is commonly used by taxpayers and charitable grantees) provided in relevant part that in the event of judicial termination of the conservation easement “the proceeds to which the Grantee shall be entitled, after the satisfaction of prior claims, . . . shall be the stipulated fair market value of this Easement.” Further, the easement deed provided that the “stipulated fair market value” of the easement at the time of any such sale would be determined as follows:

This Easement constitutes a real property interest immediately vested in Grantee, which . . . the parties stipulate to have a fair market value determined by multiplying (a) the fair market value of the Property unencumbered by this Easement (minus any increase in value after the date of this grant attributable to improvements) by (b) a fraction, the numerator of which is the value of this Easement at the time of the grant and the denominator of which is the value of the Property without deduction of the value of this Easement at the time of this grant. . . . For purposes [hereof], the ratio of the value of this Easement to the value of the Property unencumbered by this Easement shall remain constant.[] It is intended that this Section 9.2 be interpreted to adhere to and be consistent with . . . [Regulation section] 1.170A- 14(g)(6)(ii).

When the easement was granted, the improvements to the property included 20 natural gas wells, two cell phone towers, various roads, and various electrical installations. Further, other sections of the easement deed reserved to the taxpayer the right to preserve and maintain existing utility structures on the property, the right to provide underground utilities to any future permitted structures, and the right to install and maintain roads to existing structures or future improvements. The easement deed also permitted the taxpayer to access the property via an adjacent tract of land for the purpose of engaging in subsurface coal mining unless in the reasonable discretion of the grantee such activity would impair or interfere with the conservation purposes of the easement.

The appraisal relating to the conservation easement determined that the highest and best use of the property would be an “owner operated coal mining operation.” Assuming such a mining operation, the value of the property without the conservation easement was appraised at $160.5 million while the value of the property subject to the conservation easement was determined to be $5 million. The difference, $155.5 million, was the amount of the taxpayer’s claimed charitable contribution deduction. Of note, a technical report appended to the appraisal concluded that subsurface mining for coal on the property using a “room-and-pillar” technique would have “minimal” surface effects on the property. Without expressly so stating, Judge Lauber’s opinion implies that the taxpayer intended to mine coal from the property via subsurface methods notwithstanding the conservation easement.

The Service’s Position. The Service argued that the above-quoted language in the conservation easement deed failed the “extinguishment clause” requirement of Regulation section 1.170A-14(g)(6)(ii) and, thus, failed the “protected in perpetuity” rule of section 170(h)(5)(A). According to the Service, Regulation section 1.170A-14(g)(6)(ii) would require in this case that the grantee of the property receive 96.885% ($155.5 million ÷ $160.5 million) of any sales proceeds from the property if the easement was judicially extinguished. The language in the easement deed at issue, however, reduces the sales proceeds due to the grantor by “prior claims” and by “any increase in value after the date of the grant attributable to improvements.” Hence, the Service argued, the grantee would not receive 96.885% of any theoretical sales proceeds (but instead something less than 96.885%), and thus the $155.5 million charitable contribution deduction must be disallowed.

The Taxpayer’s Position. The taxpayer argued that despite any technical deficiency in the “extinguishment clause” advanced by the Service, the savings clause in the easement deed, which provided that “Section 9.2 be interpreted to adhere to and be consistent with . . . [Regulation section] 1.170A- 14(g)(6)(ii),” prevented any such technical deficiency from being fatal to the taxpayer’s charitable contribution deduction.

The Tax Court. Citing the cases mentioned above, Judge Lauber essentially agreed with the Service’s position, rejecting the taxpayer’s contention that the “savings clause” remedied any technical deficiency with the extinguishment clause in the taxpayer’s easement deed. In particular, Judge Lauber ruled that the taxpayer’s savings clause argument was inapposite for two reasons: First, the savings clause language only operates to the extent that the language of the easement deed itself is ambiguous, and in this case, Judge Lauber held that the language was unambiguous. Second, and perhaps more importantly, Judge Lauber explained that courts have routinely held such “savings clause” language to be ineffectual. Courts have declined to respect such tax-related “savings clauses” because they impose a condition subsequent—a condition that can only arise subsequent to the act (here, the conveyance) that determines the proper tax consequences of the transaction. Put differently, a savings clause cannot undo something that, from a tax standpoint, already has been done.

The Upshot. As we have seen from the decided cases, the Service takes a very dim view of conservation easements when the claimed charitable contribution deduction is far in excess of a recent acquisition price for the subject property. Even if the Service had lost its partial summary judgment motion in this case, Judge Lauber’s opinion notes that the Service would have asserted other reasons (e.g., valuation, Form 8283 deficiencies, etc.) for disallowing the $155.5 million charitable contribution deduction. Taxpayers presumably would do themselves a favor by crafting an “extinguishment clause” that forfeits to the grantee all proceeds from a judicial sale of the property. In this case, for example, it seems unlikely that the taxpayer really intended to preserve to itself 3.115% (100% – 96.885%) of the sales proceeds received in a judicial extinguishment of the conservation easement granted to the donee.

4. Taxpayers have a greater ability to deduct charitable contributions for relief efforts in areas affected by qualified disasters.

Section 204(a) of the Taxpayer Certainty and Disaster Tax Relief Act of 2019 provides special rules for charitable contributions for relief efforts in qualified disaster areas. Normally, the limit that applies to the deduction for most charitable contributions by individuals is 50% of the taxpayer’s contribution base, which, generally speaking, is adjusted gross income. Lower limits can apply depending on the type of recipient and the type of property contributed. The limit that applies to the deduction for most charitable contributions by corporations generally is ten percent of taxable income. Contributions that exceed these limits generally can be carried forward five years. The legislation provides that “qualified contributions” by an individual are not subject to the normal limits, and instead are allowed up to the amount by which the taxpayer’s contribution base (AGI) exceeds the other charitable contributions the taxpayer makes, i.e., those subject to the normal limit. In effect, this permits individual taxpayers to deduct qualified contributions up to 100% of the taxpayer’s contribution base (AGI) after taking into account other charitable contributions. For corporations, the limit on qualified contributions is the amount by which the corporation’s taxable income exceeds the corporation’s other charitable contributions, i.e., the corporation can deduct qualified contributions up to 100% of taxable income after taking into account other charitable contributions. Qualified contributions by an individual or a corporation that exceed the relevant limit can be carried forward five years.

A “qualified contribution” is defined as a charitable contribution (as defined in section 170(c)) that meets three requirements: (1) the contribution must be paid in cash to an organization described in section 170(b)(1)(A) during the period beginning on January 1, 2018, and ending on February 18, 2020 (60 days after the date of enactment), for relief efforts in a qualified disaster area, (2) the taxpayer must obtain from the organization a contemporaneous written acknowledgment that the contribution was used (or will be used) for such relief efforts, and (3) the taxpayer must elect the application of this special rule. For partnerships or S corporations, the election is made separately by each partner or shareholder. The legislation does not specify the manner of making the election. Presumably, taking the deduction on the return will constitute an election.

Several key terms are defined in section 201 of the Taxpayer Certainty and Disaster Tax Relief Act of 2019. These are as follows:

1. The term “incident period” with respect to any qualified disaster is the period specified by FEMA as the period during which the disaster occurred, except that the period cannot be treated as beginning before January 1, 2018, or ending after January 19, 2020 (the date that is 30 days after the date of enactment of the legislation).

2. The term “qualified disaster zone” is the portion of the qualified disaster area determined by the President to warrant individual or individual and public assistance from the federal government under the Robert T. Stafford Disaster Relief and Emergency Assistance Act by reason of the qualified disaster with respect to the qualified disaster area.

3. The term “qualified disaster area” is an area with respect to which the President declared a major disaster from January 1, 2018, through February 18, 2020 (the date that is 60 days after the date of enactment of the legislation), under section 401 of the Stafford Act if the incident period of the disaster began on or before December 20, 2019 (the date of enactment). To avoid providing double benefits, the legislation excludes the California wildfire disaster area, for which similar relief was provided by the Bipartisan Budget Act of 2018.

4. “The term ‘qualified disaster’ means, with respect to any qualified disaster area, the disaster by reason of which a major disaster was declared with respect to such area.”

X. Tax Procedure

A. Interest, Penalties, and Prosecutions

1. A nonprofit corporation is treated the same as a for-profit corporation.

In Judge Lynch’s opinion in Maimonides Medical Center v. United States, the Court of Appeals for the Second Circuit held that the lower interest rate under section 6621(a)(1) for a refund for an overpayment of taxes to a corporation applies to not-for-profit corporations as well as to for-profit corporations.

a. The Sixth Circuit agrees. In United States v. Detroit Medical Center, the Service refunded FICA taxes paid by the plaintiff, a not-for-profit corporation, for periods prior to April 1, 2005, following the Service’s ruling that medical residents were eligible for the student exemption from FICA taxes. The Service paid interest on the employer portion of the FICA taxes at the statutory rate provided by section 6621(a)(1) for corporations (the federal short-term rate plus two percentage points, reduced to 0.5 percentage points to the extent that the overpayment exceeds $10,000). The plaintiff asserted that because it is a nonprofit corporation, it should not be treated as a corporation for this purpose. Instead, it asserted that it was entitled to interest at the higher statutory rate provided for noncorporate taxpayers (the federal short-term rate plus three percentage points). According to the plaintiff, it was entitled to additional interest of approximately $9.1 million.

In an opinion by Judge Sutton, the Court of Appeals for the Sixth Circuit held that nonprofit corporations are “corporations” for purposes of determining the rate of interest on overpayments. Accordingly, the court affirmed the district court’s grant of the government’s motion for summary judgment.

b. The Seventh Circuit jumps on the bandwagon. In Medical College of Wisconsin Affiliate Hospitals, Inc. v. United States, a case raising the same issue, the Court of Appeals for the Seventh Circuit, in an opinion by Judge Easterbrook, concluded that a nonprofit corporation is entitled to interest on a tax overpayment at the statutory rate provided by section 6621(a)(1) for corporations.

c. The Tenth Circuit jumps on the (now overloaded?) bandwagon. In Wichita Center for Graduate Medical Education, Inc. v. United States, yet another case raising the same issue, the Court of Appeals for the Tenth Circuit, in an opinion by Judge Tymkovich, agreed that a nonprofit corporation is nonetheless a “corporation” for purposes of the lower overpayment rate of interest set forth in section 6621(a)(1).

2. Accuracy-related penalties determined by the Service’s Automated Correspondence Exam system are penalties “automatically calculated through electronic means” and therefore are not subject to the requirement of section 6751(b) that they be approved in writing by a supervisor.

In Walquist v. Commissioner, the 2014 federal income tax return filed by the taxpayers, a married couple, reflected wages and other income of $94,114 and a purported offset or deduction of $87,648, labeled as a “Remand for Lawful Money Reduction.” In addition, they failed to report $1,215 of unemployment compensation reported on Form 1099-G by the State of Minnesota. After taking into account the standard deduction, the taxpayers reported a negative taxable income of $5,731. The Service’s computer document matching system identified the return for examination, which was processed by the Service’s Automated Correspondence Exam (ACE) system. The ACE system employed the Service’s Correspondence Examination Automated Support (CEAS) software, which generated and issued to the taxpayers a Letter 525, General 30-Day Letter. The 30-day letter calculated a proposed deficiency of $13,832 and automatically calculated a 20% accuracy-related penalty of $2,766.40 pursuant to section 6662(a), (b)(2), and (d)(1)(A) for a substantial understatement of income tax. Following the taxpayers’ failure to respond to the 30-day letter, the CEAS program generated a notice of deficiency, in response to which the taxpayers filed what purported to be a petition in the Tax Court. They filed a copy of the notice of deficiency, on each page of which they had written “REFUSAL FOR CAUSE,” and attached various documents that set forth arguments commonly made by tax protestors as well as a demand that the Tax Court garnish the wages of the Secretary of the Treasury.

Among other issues in the case, the Tax Court (Judge Lauber) addressed whether the accuracy-related penalty calculated by the Service’s CEAS program was subject to the requirement of section 6751(b) that the initial determination of the assessment of a penalty be “personally approved (in writing) by the immediate supervisor of the individual making such determination.” The court held that it was not. Section 6751(b)(2) provides that supervisory approval is not required for “(A) any addition to tax under section 6651, 6654, or 6655; or (B) any other penalty automatically calculated through electronic means.” The penalty in this case, the court concluded, was determined automatically by a computer software program without the involvement of a human Service examiner and, therefore, was a penalty “automatically calculated through electronic means” within the meaning of section 6751(b)(2)(B).

The court noted that its decision is consistent with the Service’s Internal Revenue Manual, which states that substantial understatement penalties determined by the CEAS program (as well as those calculated through the Automated Underreporter program) are exempt from the supervisory approval requirement. The court also noted that its conclusion is consistent with the policy underlying the supervisory approval requirement of section 6751(b), which was enacted as a means of preventing Service employees from threatening unjustified penalties to encourage settlement. Because the supervisory approval requirement did not apply, the Service had no burden of production with respect to the penalty.

The court also imposed a penalty of $12,500 on the taxpayers pursuant to section 6673(a)(1) for advancing frivolous positions in their petition and in subsequent proceedings. The Tax Court noted its previous decision in Williams v. Commissioner that the supervisory approval requirement of section 6751(b) does not apply to the Tax Court when it imposes penalties under section 6673(a)(1).

3. The supervisory approval requirement of section 6751(b) “includes no requirement that all potential penalties be initially determined by the same individual nor at the same time,” says the Tax Court.

In Palmolive Building Investors, LLC v. Commissioner, the taxpayer, a TEFRA partnership, granted in 2004 a conservation easement valued at $257 million on the façade of the Palmolive Building on North Michigan Avenue in Chicago. In a prior opinion, the Tax Court upheld the Service’s disallowance of the taxpayer’s charitable contribution deduction on the grounds that mortgages on the building were not fully subordinated to the conservation easement, and therefore the charitable organization in whose favor the easement was granted was not, as required by relevant regulations, guaranteed the requisite share of proceeds in the event the easement was extinguished. The remaining issue was whether, in asserting certain penalties, the Service had complied with the requirement of section 6751(b) that the initial determination of the assessment of a penalty is “personally approved (in writing) by the immediate supervisor of the individual making such determination.”

During the examination of the partnership return for the year in question, the Service’s examining agent prepared Form 5701 (Notice of Proposed Adjustment) that had two Forms 886-A (Explanation of Items) attached to it. One of the Forms 886-A proposed and justified a penalty for gross valuation misstatement under section 6662(h)(1) and the other proposed and justified, in the alternative, a 20% negligence penalty under section 6662(b)(1). The agent’s supervisor signed the Form 5701. The Service issued a 30-day letter (Letter 1807) inviting the taxpayer to a closing conference to discuss the adjustments. The 30-day letter referenced only the gross valuation misstatement penalty. Subsequently, the Service issued a 60-day letter (Letter 1827) proposing adjustments and giving the taxpayer 60 days within which to file a protest with IRS Appeals. The 60-day letter had attached to it the Form 5701 and Forms 886-A. In other words, it referenced both penalties.

In IRS Appeals, the Appeals officer assigned to the case prepared a Form 5402-c (Appeals Transmittal and Case Memo) that had attached to it a proposed Notice of Final Partnership Administrative Adjustment (FPAA), the last page of which was a Form 886-A that asserted both the original penalties and, in the alternative, two additional penalties: a 20% penalty for substantial understatement of income tax under section 6662(b)(2) and a 20% penalty for substantial valuation misstatement under section 6662(b)(3). The immediate supervisor of the Appeals officer signed both the Form 5402-c and the proposed FPAA.

The Tax Court (Judge Gustafson) held that the Service had complied with the supervisory approval requirement of section 6751(b). In reaching this conclusion, the court rejected the taxpayer’s argument that the requirement had not been met with respect to the additional two penalties asserted by the Appeals officer. According to the court, “[s]ection 6751(b)(1) includes no requirement that all potential penalties be initially determined by the same individual nor at the same time.” The court also rejected the taxpayer’s argument that the supervisory approval requirement had not been met because the Service had failed to comply with certain provisions of the Internal Revenue Manual regarding documentation of penalty approval in work papers. The court emphasized that section 6751(b)(1) “does not require written supervisory approval on any particular form” and does not require the signature or written name of the person making the initial determination of the penalty.

The taxpayer also argued that the supervisory approval requirement had not been met because the Service had failed to establish when the initial determinations of the penalties were made and because the initial 30-day letter received by the taxpayer referred only to the gross valuation misstatement penalty and not to the negligence penalty. The court rejected these arguments as well. The court reasoned that the examining agent and the Appeals officer each made their initial determinations at the time they solicited their respective supervisors’ approval, and their supervisors had given the requested approval in writing.

4. Don’t think you can escape the penalty for filing an S corporation return late, even if you are the only shareholder, by requesting an extension of time to file your individual federal income tax return.

In ATL & Sons Holdings, Inc. v. Commissioner, the petitioner was a Subchapter S corporation that filed its 2012 return on Form 1120S late. The S corporation failed to request an extension of time to file its return by filing Form 7004. The sole shareholders of the S corporation were Ralph and Cassandra Allen, a married couple, who timely requested an extension of time to file their 2012 federal income tax return and who timely filed the return by the extended due date. The Service assessed a $2,340 penalty against the S corporation pursuant to section 6699 for the late filing of its return. The assessment appeared on the S corporation’s account transcript with transaction code 166, which indicated that it was a computer-generated assessment of a delinquency penalty. The S corporation had made an unspecified overpayment for 2013, which the Service credited against the 2012 penalty. The Service issued a final notice of intent to levy for the balance of the 2012 penalty, in response to which the S corporation requested a collection due process (CDP) hearing. Following the CDP hearing, which the Allens missed, but for which they submitted some additional information, the Service’s settlement officer upheld the proposed collection action and the S corporation brought a challenge in the Tax Court.

The Tax Court (Judge Gustafson) held that the settlement officer had not abused her discretion in upholding the proposed collection action and granted the Service’s motion for summary judgment. The court noted than an S corporation is an entity separate from its shareholders and is required to file its own return and to request its own extension of time to file the return. The court rejected the S corporation’s argument that the penalty should be abated because the Service had agreed to excuse the penalty under similar circumstances in a different year. The court also disagreed with the S corporation’s position that it had a good faith, reasonable cause defense to the penalty because it had only two shareholders who were aware of the S corporation’s loss for the year and that no harm had resulted from the late filing. According to the court, “[s]ection 6699 does not include a condition of harm before the penalty is imposed; it simply imposes a penalty when the filing is late (without reasonable cause).”

The court also held that the late-filing penalty of section 6699 was not subject to the requirement of section 6751(b) that the initial determination of the assessment of a penalty is “personally approved (in writing) by the immediate supervisor of the individual making such determination.” Section 6751(b)(2) provides that supervisory approval is not required for “(A) any addition to tax under section 6651, 6654, or 6655; or (B) any other penalty automatically calculated through electronic means.” The court held that the section 6699 penalty is a “penalty automatically calculated through electronic means” and, therefore, is not subject to the section 6751(b) supervisory approval requirement. The court rejected the taxpayers’ argument that, because the penalty in question is subject to a good faith, reasonable cause defense, it is not a penalty that is “automatically calculated.” “The possibility of such a defense does not change the fact that the penalty itself is automatically calculated.”

Regarding the Service’s crediting of the S corporation’s 2013 overpayment against the 2012 section 6699 penalty, the court held that the Service’s action had not violated section 6330(e)(1), which prohibits a levy before the conclusion of a CDP hearing. Although that provision prohibits collection by levy, the court stated that “[n]othing in section 6330 prohibits the Service from engaging in other nonlevy collection actions, including offsetting payments from other periods, as the Service did in this instance.”

5. No addition to tax under section 6654 will be made for farmers and fishermen for failure to make estimated income tax payments for 2018 if they file their 2018 returns and pay the total tax due by April 15, 2019 (April 17 for those in Maine and Massachusetts).

Under section 6654, individuals are required to make advance payments of their estimated income tax liability. Normally, individuals are required to make these payments in equal quarterly installments. Section 6654(a) imposes an addition to tax for failure to pay a sufficient amount of estimated income tax. Those who qualify as farmers or fishermen (generally, those for whom two-thirds of gross income is from farming or fishing) are subject to special rules under which they make only one payment, due on January 15, 2019, for the 2018 tax year, but no addition to tax is imposed for 2018 if a farmer or fisherman files a 2018 return and pays the tax shown due on the return by March 1, 2019.

Because of the magnitude of the changes enacted as part of the TCJA and the resulting difficulty farmers and fishermen encountered in estimating their income tax liability for 2018, the Service has waived the addition to tax of section 6654 for a qualifying farmer or fisherman who files his or her 2018 income tax return and pays in full any tax due by April 15, 2019 (or by April 17, 2019, for those taxpayers who live in Maine or Massachusetts) under Notice 2019-17. To request this waiver, farmers and fishermen must attach Form 2210-F, Underpayment of Estimated Tax by Farmers and Fishermen, to their 2018 tax return, which the taxpayer can do whether the return is filed electronically or on paper. Notice 2019-17 provides that a taxpayer should enter his or her name and identifying number at the top of the form and should check the waiver box (Part I, Box A). The rest of the form should be left blank.

6. No addition to tax under section 6654 will be made for failure to make estimated income tax payments if total withholding and estimated tax payments exceed 80% of the tax shown due on the 2018 return.

Under section 6654, individuals are required to make advance payments of their income tax liability either through withholding or quarterly estimated tax payments. Section 6654(a) imposes an addition to tax for failure to pay a sufficient amount of estimated income tax. No addition to tax is imposed if an individual makes payments equal to the lesser of (1) 90% of the tax shown on the return for the taxable year or (2) 100% of the tax shown on the taxpayer’s return for the preceding taxable year (110% if the individual’s adjusted gross income on the previous year’s return exceeded $150,000), as long as the preceding taxable year was a full 12 months.

Because of the magnitude of the changes enacted as part of the TCJA and the resulting difficulty taxpayers encountered in estimating their income tax liability for 2018, the Service previously issued Notice 2019-11, which waived any addition to tax under section 6654 for an individual whose total withholding and estimated tax payments made on or before January 15, 2019, equals or exceeds 85% of the tax shown on that individual’s 2018 return. In Notice 2019-25, the Service has reduced this percentage to 80%. This Notice supersedes Notice 2019-11. Accordingly, no addition to tax under section 6654 will be made with respect to an individual whose total withholding and estimated tax payments made on or before January 15, 2019, equals or exceeds 80% of the tax shown on that individual’s 2018 return.

To request a waiver under Notice 2019-25, an individual must file Form 2210, Underpayment of Estimated Tax by Individuals, Estates, and Trusts, with his or her 2018 income tax return. The form can be filed with a return filed electronically or on paper. The Notice provides further instructions regarding the completion of Form 2210. Taxpayers who are eligible for a waiver and who already have paid the addition to tax can seek a refund by filing Form 843, Claim for Refund and Request for Abatement and including the statement “80% Waiver of estimated tax penalty” on line 7.

7. Wait a minute, I thought we had a deal?! The Service can assess and collect the full amount of restitution ordered in a criminal proceeding if the restitution is due immediately, even if the district court that ordered it set a schedule of payments.

In Carpenter v. Commissioner, the taxpayer had previously agreed to plead guilty in federal district court to two counts of willfully making and subscribing to a false federal income tax return in violation of section 7206(1). The taxpayer was then sentenced to 27 months in prison and ordered to pay to the Service restitution of $507,995. According to the Tax Court, the district court’s order provided that “the restitution was ‘due and payable’ immediately and that ‘if . . . [petitioner] can’t pay’ the entire amount of restitution, he must pay $100 per month beginning 60 days after his release from imprisonment [and] continue making payments ‘until the monies are repaid.’” Following his release from prison in May 2016, the taxpayer complied with this payment schedule. Nevertheless, pursuant to section 6201(a)(4), the Service assessed the full amount of restitution that was ordered. The assessment occurred in January 2016, apparently while the taxpayer was still in prison.

The Service subsequently sent a final notice of intent to levy, which indicated that the taxpayer owed approximately $760,000. This amount represented the restitution assessed plus interest and penalties. The Service also filed a notice of federal tax lien. In response, the taxpayer requested a CDP hearing. He initially indicated that Social Security disability benefits were his only source of income and requested collection alternatives. When the Service informed him that he was ineligible for collection alternatives because he had failed to file returns for 2011 through 2015, he responded that he had mistakenly requested collection alternatives and that the Service had no authority to collect because it had not issued a notice of deficiency. Following the CDP hearing, the IRS Appeals Division issued notices of determination upholding the collection action, and the taxpayer sought review of the notices of determination in the Tax Court.

The Tax Court (Judge Cohen) held that IRS Appeals did not abuse its discretion in sustaining the collection action. In reaching this conclusion, the court considered two arguments raised by the taxpayer. First, the court rejected the taxpayer’s argument that section 6201(a)(4) does not authorize the Service to exercise administrative collection powers without obtaining a further order from the sentencing court. Section 6201(a)(4) provides in part:

The Secretary shall assess and collect the amount of restitution under an order pursuant to section 3556 of title 18, United States Code, for failure to pay any tax imposed under this title in the same manner as if such amount were such tax.
An assessment of an amount of restitution under an order described in subparagraph (A) shall not be made before all appeals of such order are concluded and the right to make all such appeals has expired.

These provisions, the court reasoned, “indicate[] that Congress intended to grant the Secretary collection authority that is independent from title 18 and the underlying criminal procedures.”

Second, the court rejected the taxpayer’s argument that the payment schedule set forth by the sentencing court limited the amount that the Service could collect. The court distinguished between restitution due immediately with a schedule of payments, such as in the taxpayer’s case, and restitution that the sentencing court expressly declines to order as due immediately. Only in the latter situation, the court reasoned, would the Service be precluded from collecting more than the amounts due under the payment schedule. The court concluded that, unless the sentencing court expressly declines to order restitution payable immediately, the court’s judgment imposes an immediate obligation on the defendant to pay the restitution. In this case, the court explained, the sentencing court did not decline to order the restitution as payable immediately, and therefore the Service could assess and collect the entire amount owed despite the schedule of payments established by the sentencing court.

However, the Service conceded and abated the assessed interest and the additions to tax for late payment based on the Tax Court’s decision in Klein v. Commissioner. In Klein, the court held that the language of section 6201(4)(A) makes clear that “[t]he amount of restitution is not a tax imposed by title 26” and that an assessment of restitution therefore does not trigger interest under section 6601(a) or an addition to tax for late payment under section 6651(a)(3). Similarly, in Muncy v. Commissioner, the Tax Court examined the language of section 6201(4) and concluded that the amount of any deficiency (as defined in section 6211(a)) for a tax year is not reduced by any criminal restitution paid. In that decision, the court noted that “[a]ny amount paid to the IRS as restitution for taxes owed must be deducted from any civil judgment the IRS obtains to collect the same tax deficiency.”

8. Sending one frivolous amended Form 1040X and later sending six photocopies of the same amended Form 1040X results in only one $5,000 frivolous return penalty, not six more.

In Kestin v. Commissioner, after correctly reporting her wages as includible in gross income on her initial federal income tax return on Form 1040, the taxpayer submitted a frivolous amended return on Form 1040X in which she reported no tax due on her wage income. The Service responded with Letter 3176C inviting the taxpayer to correct the Form 1040X to avoid a $5,000 frivolous filing penalty under section 6702(a). In response, the taxpayer sent six separate letters, each containing a photocopy of her initial Form 1040X, to various branches of the Service. This resulted in the Service imposing six additional $5,000 frivolous filing penalties. Upon her request, the Service granted the taxpayer a CDP hearing, following which the Service issued a notice of determination sustaining the imposition of all seven penalties. Dissatisfied with the outcome, the taxpayer petitioned the Tax Court pro se challenging the income tax and the six additional $5,000 penalties imposed based on the photocopies of the amended return that she had sent to the Service.

Judge Gustafson quickly rejected as frivolous the taxpayer’s claim that her wages were not includible in income and focused on whether the six additional frivolous filing penalties under section 6702(a) were warranted. The court quoted from its recent decision in Gregory v. Commissioner, in which the court had explained:

Under what is commonly called the Beard test, for example, a return must meet the following criteria: “First, there must be sufficient data to calculate tax liability; second, the document must purport to be a return; third, there must be an honest and reasonable attempt to satisfy the requirements of the tax law; and fourth, the taxpayer must execute the return under penalties of perjury.”

If a document does not constitute a “return” under the Beard test, the document might fail to trigger various results that flow from the filing of a return. For example, a document that is not a return does not start the running of the limitation period on the assessment of tax.

The court held that the taxpayer’s originally filed Form 1040X was not a return under the Beard test because it was not an “honest and reasonable attempt to satisfy the requirements of the tax law” under the third element of Beard. Nevertheless, according to the court, the frivolous filing penalty of section 6702(a) is imposed when a person files “what purports to be a return,” and because the taxpayer’s original Form 1040X purported to be a return and met the other conditions set forth in section 6702(a), the Service had correctly imposed the frivolous filing penalty with respect to this document. The court then addressed whether any of the six photocopies of the original Form 1040X “purported to be a return” within the meaning of section 6702(a). The court concluded that none of the copies purported to be a return.

The court distinguished its holding from that in Whitaker v. Commissioner, which upheld two section 6702(a) frivolous filing penalties when the taxpayer submitted two sequential Forms 1040. Each of the two Forms 1040 in Whitaker bore the taxpayer’s original signature and each had different attachments. Unlike the returns submitted in Whitaker, the taxpayer in Kestin submitted only photocopies of her returns, none of which contained an original signature and all of which were plainly marked or referenced as copies. These distinctions were sufficient for the court to hold that the photocopies did not “purport[] to be a return” and, therefore, were not subject to penalties under section 6702(a). The opinion includes a notable caveat indicating that not all copies of returns are immune from a section 6702(a) penalty. The court suggested that it could not rule out the possibility that a frivolous filing penalty would be upheld if, in response to a Service notice that no return is on file, a taxpayer submits a photocopy of a return that the taxpayer alleges to have filed previously.

The court also rejected the taxpayer’s arguments that the Service was precluded from imposing the penalties by section 6751(b). Section 6751(b) requires that the initial determination of the assessment of a penalty is “personally approved (in writing) by the immediate supervisor of the individual making such determination.” Specifically, the court held that the Letters 3176C sent by the Service inviting the taxpayer to correct her Form 1040X were not unapproved initial determinations of the penalties. The court also rejected the taxpayer’s challenges to the validity of the notice of federal tax lien and the CDP notice sent by the Service.

9. Filing an income tax return more than 60 days late just got more expensive.

Section 402 of the Setting Every Community Up for Retirement Enhancement Act of 2019 (SECURE Act) amended section 6651(a) to increase the penalty for filing an income tax return late. Prior to amendment, section 6651(a) provided that, in the case of an income tax return, if a taxpayer filed the return more than 60 days late, the minimum late-filing penalty was the lesser of $330 or 100% of the amount required to be shown as tax on the return. This legislative change increases the $330 figure to $435. Pursuant to section 6651(j)(1), the $435 figure is adjusted for inflation for returns required to be filed in a calendar year after 2020. The increased late-filing penalty applies to returns the due date for which (including extensions) is after December 31, 2019.

10. Filing certain retirement plan registration statements and returns late and for providing certain notices late is now ten times more expensive.

Section 403 of the SECURE Act amended section 6652(d), 6652(e) and 6652(h) to increase the penalties for filing certain retirement plan registration statements and returns late and for providing certain notices late. Prior to amendment, section 6652(d)(1) provided that the penalty for filing a statement required under section 6057(a) for annual registration of certain plans was $1 per participant per day with a maximum penalty of $5,000. The legislation increased these figures to $10 per participant per day with a maximum penalty of $50,000. Similarly, prior to amendment, section 6652(d)(2) provided that the penalty for filing a notification required under section 6057(b) regarding a change of status was $1 per day with a maximum penalty of $1,000. The legislation increased these figures to $10 per day with a maximum penalty of $10,000. Prior to amendment, section 6652(e) provided that the penalty for filing specified retirement plan returns late was $25 per day with a maximum penalty of $15,000. The legislation increased these figures to $250 per day with a maximum penalty of $150,000. Prior to amendment, section 6652(h) provided that the penalty for failure to provide notices required by section 3405(e)(10)(B) relating to elections regarding withholding from distributions was $10 for each failure with a maximum penalty of $5,000. The legislation increased these figures to $100 for each failure with a maximum penalty of $50,000. These changes apply to returns, statements, and notifications required to be filed, and notices required to be provided, after December 31, 2019.

B. Discovery: Summonses and FOIA

1. Nongovernment attorneys KEEP OUT!

In 2018, the Treasury Department and the Service issued Proposed Regulations that would significantly narrow final Regulations issued under section 7602 in 2016 that permit service providers with whom the Service contracts to receive books and records provided in response to a summons and participate in a summons interview. Section 6103(n) and Regulation section 301.6103(n)-1(a) permit the disclosure of returns and return information to any person for purposes of tax administration to the extent necessary in connection with the acquisition of property or certain services (such as processing, storage and reproduction) related to returns or return information. The 2016 final Regulations clarified that such persons with whom the Service or Chief Counsel contracts for services could not only receive and review books, papers, and records produced in compliance with a summons issued by the Service but also, in the presence and under the guidance of an Service officer or employee, participate fully in the interview of a witness summoned by the Service to provide testimony under oath. Commentators, including the State Bar of Texas Tax Section, had recommended removing the provisions permitting contractors to participate in a summons interview because, among other reasons, doing so would “avoid the unsettled question of whether a private contractor has the legal authority to examine a witness.”

After publishing Notice 2017-38, the Service identified eight sets of regulations that “impose an undue financial burden,” “add undue complexity,” or “exceed [the Service’s] statutory authority.” The above-mentioned final Regulations under section 7602 were one of the eight targeted for revision. Accordingly, Proposed Regulation section 301.7602-1(b)(3) provides new rules that significantly narrow the scope of the current Regulations under section 7602 by excluding nongovernment attorneys from receiving summoned books, papers, records, or other data or from participating in the interview of a witness summoned by the Service to provide testimony under oath. The Proposed Regulations contain a limited exception for an attorney hired by the Service as a specialist in foreign, state, or local law, including tax law, or in nontax substantive law that is relevant to an issue in the examination, such as patent law, property law, or environmental law, or is hired for knowledge, skills, or abilities other than providing legal services as an attorney. The Preamble to the Proposed Regulations explains the change as follows:

The Summons Interview Regulations require the Service to retain authority over important decisions when section 6103(n) contractors question witnesses, but there is a perceived risk that the Service may not be able to maintain full control over the actions of a non-government attorney hired by the Service when such an attorney, with the limited exception described below, questions witnesses. The actions of the non-governmental attorney while questioning witnesses could foreclose IRS officials from independently exercising their judgment. Managing an examination or summons interview is therefore best exercised solely by government employees, including government attorneys, whose only duty is to serve the public interest. These concerns outweigh the countervailing need for the Service to use non-government attorneys, except in the limited circumstances set forth in proposed paragraph (b)(3)(ii). Treasury and the Service remain confident that the core functions of questioning witnesses and conducting examinations are well within the expertise and ability of government attorneys and examination agents.

The Proposed Regulations apply to examinations begun or administrative summonses served by the Service on or after March 27, 2018.

The Service’s position in the Proposed Regulations represents a change in policy. The Service made a controversial decision to engage the law firm Quinn Emanuel Urquhart & Sullivan, LLP, as a private contractor to assist in the Service’s examination of Microsoft’s 2004 to 2006 tax years. A federal district court expressed concern about this practice, but upheld enforcement of the summonses issued by the Service to Microsoft.

a. Congress has stepped in to narrow the information the Service can provide to a tax administration contractor and to prohibit such contractors from questioning a witness under oath whose testimony was obtained by summons. Section 1208 of the Taxpayer First Act amends section 7602 by adding new section 7602(f), which provides that the Service shall not, under the authority of section 6103(n), provide to any tax administration contractor any books, papers, records, or other data obtained by summons, “except when such person requires such information for the sole purpose of providing expert evaluation and assistance to the IRS.” The legislation also provides that no person other than an employee of the Service or the Office of Chief Counsel may question a witness under oath if the witness’s testimony was obtained by summons. These changes are effective on July 1, 2019, the date of enactment.

2. A John Doe summons must seek information that is narrowly tailored and that pertains to the failure of the targeted person or group to comply with the internal revenue laws.

A summons that does not identify the taxpayer whose liability is being investigated is commonly referred to as a “John Doe” summons. For example, the Service might issue a summons to credit card companies to obtain customer records of unnamed United States taxpayers with accounts in certain countries. Because the person being investigated has no opportunity to seek to quash the summons or intervene in an enforcement proceeding, section 7609(f) requires the Service to obtain judicial approval before issuing the summons. According to section 7609(f), in the judicial proceeding, the Service must establish that:

  1. the summons relates to the investigation of a particular person or ascertainable group or class of persons,
  2. there is a reasonable basis for believing that such person or group or class of persons may fail or may have failed to comply with any provision of any internal revenue law, and
  3. the information sought to be obtained from the examination of the records or testimony (and the identity of the person or persons with respect to whose liability the summons is issued) is not readily available from other sources.

Section 1204 of the Taxpayer First Act amends section 7609(f) to preclude the Service from issuing a John Doe summons unless the information sought to be obtained is narrowly tailored and pertains to the failure (or potential failure) of the relevant person or group or class of persons to comply with one or more provisions of the internal revenue law that have been identified. This change applies to summonses served after August 15, 2019 (the date that is 45 days after the date of enactment).

C. Litigation Costs

There were no significant developments regarding this topic during 2019.

D. Statutory Notice of Deficiency

1. ♪♫ If you want my love, leave your name and address . . . ♫♪ A notice of deficiency was mailed to the taxpayers’ last known address as included on the taxpayers’ tax return, despite their filing of a power of attorney and a request for an extension using their new address.

Section 6212(b)(1) provides that a “notice of a deficiency in respect of a tax imposed by subtitle A . . . shall be sufficient . . . if mailed to the taxpayer at his last known address.” For this purpose, a taxpayer’s last known address is “the address that appears on the taxpayer’s most recently filed and properly processed Federal tax return, unless the [Service] is given clear and concise notification of a different address.”

In Gregory v. Commissioner, the taxpayers, a married couple, moved from Jersey City, New Jersey, to Rutherford, New Jersey, on June 30, 2015. They filed their 2014 federal income tax return on October 15, 2015. The return incorrectly reflected their old Jersey City address. In November 2015, they submitted a power of attorney, Form 2848, to the Service that had their new Rutherford address. In April 2016, they filed a request for an automatic extension of time to file their 2015 federal income tax return, Form 4868, that also had their new Rutherford address. The Service sent a notice of deficiency with respect to the 2014 tax year by certified mail to the taxpayers’ old address, in Jersey City, on October 13, 2016. The U.S. Postal Service returned the notice of deficiency to the Service as unclaimed. The taxpayers first became aware of the notice of deficiency on January 17, 2017, and, in response, filed a petition in the Tax Court that same day. The Service moved to dismiss for lack of jurisdiction because the taxpayers had filed their petition late (outside the 90-day time period of section 6213(a)), and the taxpayers moved to dismiss for lack of jurisdiction on the grounds that the notice of deficiency was invalid since it had not been mailed to their last known address.

The Tax Court (Judge Buch) held that the notice of deficiency was mailed to the taxpayers’ last known address and granted the government’s motion to dismiss. The court first reasoned that neither the Form 2848 nor the Form 4868 submitted by the taxpayers was a “return” within the meaning of the last known address rule of Regulation section 301.6212-2(a). These forms, the court reasoned, are not returns under the four-part test of Beard v. Commissioner. Further, the court explained, additional information on what constitutes a return for purposes of the last known address rule can be found in revenue procedures published by the Service. That these forms do not constitute clear and concise notification of a new address, the court explained, is implicit in Revenue Procedure 2010-16, which provides that Forms 2848 and 4868 are not returns and that they “will not be used by the Service to update the taxpayer’s address of record.” Finally, the court distinguished earlier decisions holding that a Form 2848 filed with the Service gave clear and concise notification of a new address. The court reasoned that these decisions were based on prior versions of Form 2848 and that “[s]ince 2004 the Commissioner has issued clear guidance informing taxpayers of what actions will and will not change their last known address with the Commissioner.”

The taxpayers have appealed this decision to the Court of Appeals for the Third Circuit, the same court that held, in Expanding Envelope & Folder Corp. v. Shotz, that a prior version of Form 2848 provided clear and concise notification of a taxpayer’s new address. Stay tuned.

2. ♪♫Should I stay or should I go? ♫♪ A divided Tax Court has held that a notice of deficiency mailed to a corporate taxpayer, the initial pages of which identified the taxpayer but the latter pages of which identified a related entity, was not a valid notice of deficiency and, therefore, did not confer jurisdiction on the Tax Court.

In U.S. Auto Sales, Inc. v. Commissioner, the Service mailed to the taxpayer a notice of deficiency dated May 15, 2012. This notice of deficiency determined deficiencies of approximately $24,000 and $31,000 for the taxable years ending June 30, 2003 and 2007, respectively. The notice of deficiency was an eleven-page document, the first four pages of which identified the taxpayer and the remaining seven pages of which identified a related entity, U.S. Auto Finance, as the taxpayer. The Service mailed to the taxpayer a second notice of deficiency dated August 2, 2012. This notice of deficiency identified only the taxpayer and determined deficiencies for the taxable years ending June 30, 2007 and 2008 of approximately $3.4 million and $3 million, respectively. The taxpayer filed timely petitions in the Tax Court in response to both notices of deficiency. The Service moved to dismiss on the ground that the first (May 15) notice of deficiency failed to identify a specific taxpayer and, therefore, was not a valid notice of deficiency that could confer jurisdiction on the Tax Court. The taxpayer argued that the May notice of deficiency was valid.

In a reviewed opinion (9–0–6) by Judge Marvel, the Tax Court held that the May notice of deficiency was invalid and granted the Service’s motion to dismiss. For guidance on the validity of a notice of deficiency, the court relied on its prior opinion in Dees v. Commissioner. In Dees, the court reviewed its prior decisions regarding the validity of notices of deficiency and framed the analysis as follows:

In the holdings of these cases we see a two-pronged approach to the question of the validity of the notice of deficiency.

First, we look to see whether the notice objectively put a reasonable taxpayer on notice that the Commissioner determined a deficiency in tax for a particular year and amount. If the notice, viewed objectively, sets forth this information, then it is a valid notice. . . . Accordingly, if the notice is sufficient to inform a reasonable taxpayer that the Commissioner has determined a deficiency, our inquiry ends there; the notice is valid.

But what if, as here, the notice is ambiguous? Then our caselaw requires the party seeking to establish jurisdiction to establish that the Commissioner made a determination and that the taxpayer was not misled by the ambiguous notice.

In U.S. Auto Sales, Inc., the court concluded that the May notice of deficiency was ambiguous under the first step of the two-step analysis required by Dees. The cover letter and the Form 4089 (Notice of Deficiency-Waiver) identified the taxpayer but the Form 5278 statement of changes and the Form 886-A explanation of changes identified the related entity. The court characterized the notice as “fatally inconsistent as to the identity of the taxpayer against whom the deficiencies are determined” and therefore ambiguous.

In the second step of the Dees two-step analysis, the taxpayer, as the party seeking to establish jurisdiction, bore the burden of proving that the May notice reflected a determination with respect to the taxpayer. According to the court, the taxpayer had failed to meet this burden. The court indicated that, in step two of the Dees analysis, it “may consider evidence from outside the four corners of the notice to establish whether the Commissioner made a taxpayer-specific determination.” The Service relied on the taxpayer’s tax returns, which were introduced in support of the government’s motion to dismiss, to support its argument that the May notice could not have related to the taxpayer. The taxpayer admitted that the May notice reflected determinations with respect to its related entity, U.S. Auto Finance, and the court concluded that it was “clear that petitioner has not been prejudiced by the erroneous notice.” In concluding that the taxpayer had failed to meet its burden in this second step, the court rejected the taxpayer’s argument that Benzvi v. Commissioner, a decision of the Court of Appeals for the Eleventh Circuit, to which the case was appealable, did not require a notice of deficiency to identify a specific taxpayer in order to be valid.

a. Concurring opinion of Judges Marvel and Lauber. Judges Marvel and Lauber wrote a concurring opinion joined by Judges Thornton, Buch and Copeland. The opinion responds to a harshly worded dissenting opinion of Chief Judge Foley and Judge Urda, which suggests that the court’s opinion “bends over backward to clean up the IRS’s mess.” The concurring opinion emphasizes that the controlling precedent is Dees and not, as the dissent contends, the court’s opinion in Scar v. Commissioner. In Scar, the Tax Court had upheld the validity of a notice of deficiency, but the Ninth Circuit reversed and held that the notice was invalid for lack of a “determination” because it was based on a tax shelter partnership in which the taxpayers were not partners and calculated tax at the highest marginal rate rather than the actual rates applicable to the taxpayers. Judges Marvel and Lauber characterized the notice of deficiency in Scar as one that “did not involve an ambiguity regarding the identity of the taxpayer against whom the deficiency was determined,” but rather as one that “did not involve a determination at all, at least according to the U.S. Court of Appeals for the Ninth Circuit . . . .”

b. Concurring opinion of Judge Buch. Judge Buch wrote a concurring opinion joined by Judges Marvel, Paris, Lauber, Nega, and Copeland. Judge Buch also emphasized that Scar is “inapposite.” He expressed the view that Scar might be considered controlling if this case, which is appealable to the Eleventh Circuit, were instead appealable to the Ninth Circuit. But the notice of deficiency in this case, unlike the notice of deficiency in Scar, he emphasized, “is ambiguous as to perhaps the most critical element of such a notice: the identity of the taxpayer about whom the Commissioner determined a deficiency.” The court’s decision in Dees, he stated, sets forth the framework for deciding whether the notice of deficiency is valid.

c. Dissenting opinion of Chief Judge Foley and Judge Urda. Chief Judge Foley and Judge Urda wrote a dissenting opinion joined by Judges Gale, Gustafson, Pugh, and Ashford. The opinion argues that the notice of deficiency in this case satisfied the “minimal jurisdictional hurdles,” which are that “[t]he notice must advise a taxpayer that the IRS has determined a deficiency for a specific year and in a particular amount.” The dissenting opinion also argues that the Tax Court’s opinion in Scar (referred to as Scar I) is the controlling precedent and that the situation in Dees, in which the notice of deficiency stated that the deficiency that had been determined was zero, “does not resemble this case.” The dissenting opinion rejects as unconvincing the position set forth in the concurring opinions that this case is distinguishable from Scar because it involves an ambiguity as to the identity of the taxpayer. Judges Foley and Urda also expressed concern that the approach set forth in the court’s opinion “contemplates an examination of extrinsic evidence in order to decide our jurisdiction.” Under the court’s approach, they stated, “[u]nless the notice indubitably demonstrates that a deficiency determination has been made, we are to rifle through extrinsic evidence to sniff out what really happened.” Such an approach, they argued, is neither warranted by precedent nor prudent. They argued that the court’s approach should be much simpler:

In other words, once the IRS sends a taxpayer a slip of paper informing the taxpayer that the IRS has determined a deficiency against it for a particular year, that taxpayer can come to this Court to challenge the determination.

The dissenting opinion also argues that the concurring opinions had failed to address fully the court’s opinion in Campbell v. Commissioner:

[I]n attempting to dodge Scar I, the concurrences fail to fully take into account Campbell. In that case, the IRS sent a deficiency notice in which the first two pages related to the Campbells and the attachments related to a person named Dan Daigle. . . . We did not treat the notice as ambiguous. Rather, we concluded that the notice did not reveal on its face that the IRS had failed to make a determination and exercised jurisdiction.

The better approach, the dissent argued, would be to hold that the notice of deficiency was valid, freely allow the Service to amend its answer, and for the court to resolve the issues.

d. Dissenting opinion of Judge Ashford. Judge Ashford wrote a dissenting opinion in which she argued, as she did in her concurring opinion in Dees, that the relevant statutory provisions, sections 6212, 6213 and 6214, do not support the two-step analysis of Dees. Judge Ashford distinguished between the Service’s determination of a deficiency and its issuance of the notice of deficiency. In her view, it is the Service’s determination of a deficiency that confers jurisdiction on the Tax Court.

[W]e have jurisdiction over a deficiency determination, as a substantive matter, regardless of whether the notice of deficiency understandably reflects it or not, as long as a notice of deficiency was in fact issued, as a procedural matter.

Judge Ashford expressed the view that the appropriate remedy for a notice of deficiency with inadequate information is not to decline jurisdiction over the case, but to shift to the Service the burden of proof on any matter not reflected in the notice or stated incorrectly in the notice.

E. Statute of Limitations

1. A district court has declined to dismiss a taxpayer’s refund action as untimely despite the taxpayer’s failure to submit the specific documentation required by Revenue Procedure 99-21.

In Stauffer v. Internal Revenue Service, the taxpayer did not file federal income tax returns for the years 2006 through 2012. Upon the taxpayer’s death at the age of 90 in 2012, his son was appointed as administrator of the estate. As administrator, the son filed the missing returns and sought a refund of tax for the year 2006 of more than $137,000. The Service denied the claim as untimely under section 6511. Section 6511(a) provides that a claim for refund must be filed within the later of two years from the time the tax was paid or three years from the time the return was filed. The taxpayer’s claims for refund were filed within three years of the time the returns were filed (and therefore were timely under section 6511(a)) because they were submitted simultaneously with the returns. However, section 6511(b)(2)(A) provides that, when a claim for refund is timely under the three-years-from-filing period of section 6511(a), the taxpayer can recover only the portion of the tax paid within the three-year period ending on the date the claim for refund was filed (plus the period of any extension the taxpayer obtained). In this case, section 6511(b)(2)(A) barred the taxpayer from obtaining the 2006 refund because the taxpayer had paid all of the tax more than three years before the claims for refund were filed.

The taxpayer, through his son as administrator, asserted that, notwithstanding the normal limitations periods, he was entitled to relief under section 6511(h)(1), which suspends the running of the periods in section 6511(a), (b), and (c) during any period that the taxpayer is “financially disabled.” The term “financially disabled” is defined under section 6511(h)(2) as being “unable to manage his financial affairs by reason of a medically determinable physical or mental impairment of the individual which can be expected to result in death or which has lasted or can be expected to last for a continuous period of not less than 12 months.” The son filed an administrative appeal and asserted that the limitations periods of section 6511 had been tolled because his father had been financially disabled within the meaning of section 6511(h). With the administrative appeal, the son submitted a statement from the taxpayer’s psychologist attesting that the taxpayer had suffered from a variety of ailments that had affected his mental capacity and had prevented him from managing his financial affairs from at least 2006 until his death in 2012.

The Service’s guidance on section 6511(h) is set forth in Revenue Procedure 99-21. The Revenue Procedure requires, among other things, that the taxpayer submit (1) a physician’s statement attesting to the specific time period during which the physical or mental impairment prevented the taxpayer from managing his or her financial affairs and (2) a statement that no person was authorized to act on the taxpayer’s behalf in financial matters during the specified period of disability. The Revenue Procedure provides that the term “physician” has the same meaning as that in section 1861(r)(1) of the Social Security Act, 42 U.S.C. section 1395x(r), which sets forth five categories of professionals considered to be physicians, none of which includes psychologists. The Service concluded that the taxpayer had not complied with the requirement of Revenue Procedure 99-21 that the taxpayer submit the statement of a “physician” and denied the claim as untimely.

The district court (Judge Wolf) held that the Service had failed to establish that its adoption of the Social Security Act’s definition of a physician in Revenue Procedure 99-21 was the product of reasoned decision making as required by section 706(2)(A) of the Administrative Procedure Act and the Supreme Court’s decision in Motor Vehicle Manufacturers Association of the United States v. State Farm Mutual Automobile Insurance Co.

The government . . . has not submitted any evidence of the IRS’s rationale in adopting the definition in 42 U.S.C. § 1395x(r). . . . The IRS, therefore, has not provided any explanation for its decision, let alone a “rational connection between the facts found and the choice made.” State Farm, 463 U.S. at 43. The IRS may conceivably view doctors without medical degrees to be generally unqualified to make the determination required under section 6511, and may have determined that, in view of the “need to fairly and efficiently process a potentially large number of [refund] claims,” Abston, 691 F.3d at 996, a case-by-case determination of whether a given psychologist is nevertheless qualified is unwarranted. However, as explained earlier, at least where the IRS’s reasoning is not obvious, the court may not supply an explanation for the IRS’s choice that the agency itself has not given. See State Farm, 463 U.S. at 43.

The court also rejected the government’s argument that the taxpayer was not entitled to relief under section 6511(h) because the taxpayer had submitted the psychologist’s statement in the course of the administrative appeal, rather than with the claim for refund as required by Revenue Procedure 99-21. When refund claims are technically deficient, the court noted, courts generally accept the missing information at a later stage. Accordingly, the court denied the government’s motion to dismiss without prejudice.

a. But the same district court has dismissed the taxpayer’s refund action as untimely on the basis that his son was authorized to act for him for a period of time and therefore he was not “financially disabled” within the meaning of section 6511(h) during that period. In Stauffer v. Internal Revenue Service, the government again moved to dismiss as untimely the taxpayer’s complaint seeking a tax refund for the year 2006. The government argued that the running of the limitations period on seeking a tax refund for that year was not tolled on the basis of the taxpayer being “financially disabled” within the meaning of section 6511(h). Under section 6511(h)(2)(B), “[a]n individual shall not be treated as financially disabled during any period that such individual’s spouse or any other person is authorized to act on behalf of such individual in financial matters.” (This same requirement is reflected in Revenue Procedure 99-21, which provides that, to obtain relief under section 6511(h), the taxpayer must submit a statement that no person was authorized to act on the taxpayer’s behalf in financial matters during the specified period of disability.)

The district court (Judge Wolf) found that the taxpayer’s son had authority pursuant to a durable power of attorney (POA) to act on his father’s behalf in financial matters from October 2005 until his father’s death in October 2012. Although the son had had a falling out with his father and had told his father “that he would no longer be exercising any rights granted to him under the [Durable] POA,” he later reconciled with this father and exercised powers under the power of attorney. The court concluded that the son had never effectively renounced the power of attorney. The court rejected the taxpayer’s argument that a person should be considered “authorized” to act on the taxpayer’s behalf within the meaning of section 6511(h)(2)(B) only when that person has a duty to act on the taxpayer’s behalf and knowledge that action is necessary, i.e., a duty to file tax returns claiming refunds and knowledge that such returns have not been filed. Accordingly, the court concluded that, because the limitations period on seeking a tax refund was not tolled, the taxpayer’s refund claim was untimely and granted the government’s motion to dismiss.

The result in this case is consistent with that in Estate of Kirsch v. United States, in which the court held that the period of limitations on seeking a tax refund was not tolled due to the taxpayer’s financial disability under section 6511(h) because the taxpayer’s son held a durable power of attorney authorizing him to act on behalf of the taxpayer, his mother.

b. The First Circuit has affirmed and concluded that the limitations period on seeking a tax refund was not tolled by reason of the taxpayer’s financial disability. In an opinion by Judge Torruella, the Court of Appeals for the First Circuit has affirmed the district court’s dismissal of the taxpayer’s refund action. Like the district court, the First Circuit concluded that the taxpayer’s son was authorized to act for the taxpayer in financial matters within the meaning of section 6511(h)(2)(B) and that the taxpayer therefore was not financially disabled. The court also concluded that the father had never revoked the power of attorney and that the son had never renounced it.

The taxpayer argued that a person should be treated as authorized to act on the taxpayer’s behalf in financial matters within the meaning of section 6511(h)(2)(B) “only if he or she has: (1) authority to file the financially disabled taxpayer’s tax returns; (2) a duty to file the financially disabled taxpayer’s tax returns; and (3) actual or constructive knowledge that the tax returns for a particular year have to be filed on behalf of the disabled taxpayer.” The court concluded that it did not need to decide whether the first proposed requirement must be met because, even if it is required, the power of attorney in this case explicitly gave the son authority to file his father’s tax returns. The court rejected the latter two proposed requirements on the ground that they “find[] no support in § 6511(h)(2)(B)’s plain language or its statutory context.” Because the taxpayer was not financially disabled within the meaning of section 6511(h), the taxpayer’s refund claim was untimely, and the court affirmed the district court’s grant of the government’s motion to dismiss for lack of subject-matter jurisdiction.

2. Shouldn’t the limitation period on seeking tax refunds be simpler than it currently is? A taxpayer lost the ability to obtain a refund because of a limit on the amount of tax recoverable.

In Borenstein v. Commissioner, the taxpayer filed a timely extension request for her 2012 federal income tax return and paid a total of $112,000 towards her 2012 federal tax liability. All of her payments, made through estimated tax payments and a payment with her extension request, were deemed to be made on April 15, 2013. She did not file her 2012 return until August 29, 2015, after she had received a notice of deficiency for 2012. Her return reflected a tax liability of $79,559, which the Service agreed was correct. Thus, she had overpaid her 2012 federal tax liability by $32,441. In response to the notice of deficiency, the taxpayer filed a petition in the Tax Court.

Under section 6512(b)(1), the Tax Court has jurisdiction to determine an overpayment if it has jurisdiction by virtue of a notice of deficiency. In this case, the court had deficiency jurisdiction because the Service had issued a notice of deficiency and the taxpayer had filed a timely petition. Section 6512(b)(3), however, imposes a limit on the amount of tax that can be refunded. This provision states that only the portion of the tax paid within one of three specific time periods is allowed as a credit or refund. The parties agreed that the relevant period was that set forth in section 6512(b)(3)(B), which refers to tax paid “within the period which would be applicable under section 6511(b)(2), (c), or (d), if on the date of the mailing of the notice of deficiency a claim had been filed (whether or not filed) stating the grounds upon which the Tax Court finds that there is an overpayment.” In other words, the court must treat the taxpayer as having filed a hypothetical claim for refund on the date the notice of deficiency was mailed. The question is, taking into account the limits of section 6511(b)(2), (c), or (d), what amount might have been recovered through this hypothetical refund claim? Of these limits, only section 6511(b)(2) was relevant. This provision states that a taxpayer can recover tax paid within either a two-year or a three-year period ending on the date the taxpayer filed the claim for refund. The three-year look-back period applies when the taxpayer files the refund claim “within 3 years from the time the return was filed.” The two-year look-back period applies in all other cases.

The issue before the court was whether the taxpayer was entitled to a credit or refund of the overpayment. The Tax Court (Judge Lauber) held that she was not. In this case, the court reasoned, section 6512(b)(3)(B) treats the hypothetical refund claim as having been filed on June 19, 2015, the date on which the notice of deficiency was mailed. This was before the taxpayer had filed her return for the year. Accordingly, the court held, the hypothetical refund claim could not be regarded as having been filed “within 3 years from the time the return was filed,” and therefore the amount of tax recoverable was limited to the portion paid within the two-year period preceding June 19, 2015. All of the tax in question was deemed paid on April 15, 2013, and therefore, the taxpayer was not entitled to a refund of any of the tax paid.

In reaching this conclusion, the court rejected arguments made by the taxpayer that a three-year look-back period applied by virtue of the final sentence of section 6512(b)(3), which states:

[W]here the date of the mailing of the notice of deficiency is during the third year after the due date (with extensions) for filing the return of tax and no return was filed before such date, the applicable period under subsections (a) and (b)(2) of section 6511 shall be 3 years.

Congress added this flush language to the statute to overturn the Supreme Court’s decision in Commissioner v. Lundy, in which the Court had held that, when a taxpayer has not filed a return, only a two-year look-back period (not a two- or three-year, whichever is later, look-back period) applies. The Tax Court agreed with the Service that the parenthetical expression “(with extensions)” in the flush language of section 6512(b)(3) modifies the term “due date.” The extended due date was October 15, 2013. The court reasoned that “the third year” referred to in section 6512(b)(3)(B) began on October 15, 2015. The Service mailed the notice of deficiency on June 19, 2015, which was, the court concluded, during the second year after the extended due date, not the third year. Accordingly, the flush language of section 6512(b)(3), in the Tax Court’s view, did not trigger a three-year look-back period. In reaching this conclusion, the court rejected the argument of the amici curiae that the Service’s interpretation of the statute created a six-month jurisdictional “black hole” into which the taxpayer’s refund claim disappeared. That turn of phrase apparently resonated with the Second Circuit on appeal, as explained below.

a. The Second Circuit has reversed the Tax Court’s decision. In Borenstein v. Commissioner, the Court of Appeals for the Second Circuit (Judge Jacobs) reversed the Tax Court’s decision and held that the parenthetical expression “(with extensions)” in the flush language of section 6512(b)(3) does not create a six-month “black hole” for jurisdiction regarding refund claims asserted in the Tax Court. Instead, according to the court, the “(with extensions)” language modifies the phrase “third year after the due date.” In this case, this interpretation has the effect of adding six months to the three-year look-back period beginning on the date on which the Service mailed the notice of deficiency. A look-back period of three years and six months that ends on June 19, 2015, extends back to December 19, 2012. Because all of the tax in question was deemed paid on April 15, 2013, which was well within the look-back period, the Tax Court could order a refund of the taxpayer’s overpayment with respect to the 2012 tax year. Judge Jacobs reasoned that such an interpretation of the statutory language was consistent with Congressional intent in overturning Lundy, and it is also supported by the longstanding canon of statutory construction that resolves ambiguities in favor of taxpayers and against the government.

2. The common-law mailbox rule was displaced by regulations, says the Ninth Circuit.

In Baldwin v. United States, the taxpayers, a married couple, filed a return for 2007 that reflected a net operating loss. They wished to carry this loss back to 2005 and, under the relevant statutory provisions (section 6511(b)(1), (d)(2)(A)), in order to obtain a refund of taxes paid with respect to 2005, were required to file a claim for refund by October 5, 2011. The taxpayers asserted that they had filed an amended return seeking a refund for 2005 in June 2011. The Service, however, never received that amended return. The Service received the taxpayers’ 2005 amended return in 2013 after the limitation period for seeking a refund had expired, and the Service, therefore, denied their refund claim. The taxpayers then brought an action for a refund in the federal district court.

Under section 7422(a), the jurisdiction of both the district courts and the Court of Federal Claims to hear tax refund actions is limited to those cases in which the taxpayer has “duly filed” a claim for refund with the Service. The issue, in this case, was how the taxpayers could prove that they had filed the necessary and timely refund claim. Under the common-law mailbox rule, developed and applied by some courts, “proof of proper mailing—including by testimonial or circumstantial evidence—gives rise to a rebuttable presumption that the document was physically delivered to the addressee in the time such a mailing would ordinarily take to arrive.” At trial, the taxpayers introduced the testimony of two of their employees that they had deposited the amended 2005 return in the mail at the post office in Hartford, Connecticut, on June 21, 2011. The district court credited the testimony of the two employees, applied the common-law mailbox rule, and held that the taxpayers were entitled to a refund of approximately $167,000 plus litigation costs of $25,000.

In an opinion by Judge Watford, the Court of Appeals for the Ninth Circuit reversed. The common-law mailbox rule, the court held, was displaced by section 7502. Under section 7502(a), the postmark stamped on the cover in which a return or claim is mailed is deemed to be the date of delivery if the return or claim (1) is deposited in the mail in the United States within the time prescribed for filing in a properly addressed, postage prepaid envelope or other appropriate wrapper and bears a postmark date that falls within the time prescribed for filing and (2) is delivered by United States mail after the prescribed time for filing to the agency with which it is required to be filed. The statute also provides that, if the return or claim is mailed by United States registered mail, the date of registration is treated as the postmark date, and the registration is prima facie evidence that the return or claim was delivered to the agency to which it was addressed.

Section 7502(c)(2) authorizes the Secretary of the Treasury to issue regulations providing the same treatment of returns or claims sent by certified mail, which the Treasury Department and the Service have done. Regulation section 301.7502-1(e)(2)(i) provides that, except for direct proof of actual delivery, proof of proper use of registered or certified mail (or a designated private delivery service) is the exclusive means to establish prima facie evidence of delivery and that “[n]o other evidence of a postmark or of mailing will be prima facie evidence of delivery or raise a presumption that the document was delivered.”

The Ninth Circuit assessed the validity of the Regulation by applying the two-step analysis of Chevron U.S.A., Inc. v. Natural Resources Defense Council, Inc. The court concluded in Chevron step one that the statute, section 7502, is silent as to whether it displaces the common-law mailbox rule with respect to items sent by regular mail, and in step two Regulation section 301.7502-1(e)(2)(i) is a permissible interpretation of the statute. Accordingly, the court deferred to the regulatory interpretation of the statute and held that, because section 7502 displaces the common-law mailbox rule, the taxpayers could not rely on the testimony of their employees to raise a presumption that their refund claim was delivered.

In Anderson v. United States, the Ninth Circuit had previously held that section 7502 did not displace the common-law mailbox rule. Despite that prior decision, the court upheld the validity of the regulation by applying the rule of National Cable & Telecomm. Association v. Brand X Internet Services, which held that a court’s prior judicial construction of a statute trumps an agency construction that is entitled to Chevron deference only if the prior court’s decision holds that its construction follows from the unambiguous terms of the statute and leaves no room for agency discretion. The Ninth Circuit’s decision in Anderson did not express such a holding. Prior to the Treasury Department’s issuance of Regulation section 301.7502-1(e)(2)(i), other federal courts of appeal had split on the issue of whether section 7502 displaced the common-law mailbox rule. It seems likely that, if the issue arises in these courts with respect to a year subject to the Regulation, they will follow the Ninth Circuit in giving Chevron deference to the Regulation.

3. The taxpayers missed an opportunity to challenge the Tax Court’s decision in Allen v. Commissioner, which held that the fraud exception to the three-year limitation period on assessment is triggered by a return preparer’s fraudulent intent.

Generally, under section 6501(a) the Service must assess additional tax within three years after the return for the year in question is filed. Before assessing additional tax, the Service generally must issue a notice of deficiency, which provides the taxpayer with 90 days within which to file a petition in the Tax Court.

In Finnegan v. Commissioner, the Service issued a notice of deficiency with respect to the returns of the taxpayers, a married couple, for the years 1994 through 2001, more than three years after the returns were filed. The Service argued that the notice of deficiency was timely under the fraud exception of section 6501(c)(1), which provides that tax may be assessed at any time “[i]n the case of a false or fraudulent return with the intent to evade tax.” The Service’s theory was that the taxpayers’ return preparer had filed false or fraudulent returns for the taxpayers. Their returns included inappropriate items such as losses from a partnership of which they had never heard. According to the court, the taxpayers “apparently were oblivious” to the inappropriate items on their returns. A Service investigation of the return preparer revealed that he and his associates had filed 750 to 800 fraudulent returns every year for 11 years. The return preparer was indicted and pled guilty to conspiring to defraud the United States and interfering with the administration of the internal revenue laws. The Service relied on Allen v. Commissioner, in which the Tax Court had held that “[n]othing in the plain meaning of the statute [section 6501(c)(1)] suggests the limitation[] period is extended only in the case of the taxpayer’s fraud. The statute keys the extension to the fraudulent nature of the return, not to the identity of the perpetrator of the fraud.”

At trial in the Tax Court, the Service introduced the return preparer’s prior testimony that every return he prepared during the relevant period was fraudulent. The Service also presented an affidavit of the return preparer in which he swore that he had knowingly prepared fraudulent returns for the taxpayers. At trial, the taxpayers conceded that if their returns were fraudulent, then pursuant to section 6501(c)(1) the Service could assess tax at any time. The Tax Court (Judge Wells) held that the fraud exception was triggered and ruled in favor of the Service. With the assistance of new counsel, the taxpayers filed a motion for reconsideration and argued for the first time that the fraudulent intent of a return preparer (rather than of the taxpayer) could not trigger the fraud exception. In other words, the taxpayers asked the Tax Court to reconsider its decision in Allen. The Tax Court declined to consider this argument because it was raised for the first time in the taxpayers’ motion for reconsideration.

In an opinion by Judge Tjoflat, the Court of Appeals for the Eleventh Circuit affirmed the Tax Court’s decision. The taxpayers argued that they had not waived their challenge of the Allen decision because the applicability of a statute of limitation is not savable and because the Tax Court had considered their challenge and issued a decision. The Eleventh Circuit rejected these arguments and also declined to exercise its discretion to consider an issue raised for the first time on appeal. The Eleventh Circuit also rejected the taxpayers’ challenge to the Tax Court’s admission into evidence of the return preparer’s prior testimony concerning his preparation of fraudulent returns and his affidavit regarding the preparation of the taxpayers’ returns. The Tax Court had concluded that these statements qualified for the statement-against-interest exception to the hearsay rule, and the Eleventh Circuit agreed.

5. A mandatory 60-day extension of certain deadlines for those affected by federally declared disasters.

Section 205 of the Taxpayer Certainty and Disaster Tax Relief Act of 2019 provides a mandatory 60-day extension of certain deadlines for those affected by federally declared natural disasters. Prior to the legislation, section 7508A(a) authorized the Secretary of the Treasury to specify a period of time of up to one year that is disregarded in determining an affected taxpayer’s compliance with deadlines such as those for filing returns and paying tax, an affected taxpayer’s liability for interest and penalties, and an affected taxpayer’s entitlement to a credit or refund. The legislation adds new section 7508A(d), which provides a mandatory 60-day extension for qualified taxpayers. A qualified taxpayer is defined to include those whose principal residence or principal place of business (other than performing services as an employee) is located in a disaster area, relief workers working for recognized government or philanthropic organizations to assist in a disaster area, those whose records are located in a disaster area, and those visiting a disaster area who are killed or injured as a result of the disaster. For this purpose, the term “disaster area” is defined in section 165(i)(5), which generally defines a disaster area as any area determined to warrant assistance by reason of any disaster determined by the President to warrant assistance by the federal government under the Robert T. Stafford Disaster Relief and Emergency Assistance Act.

F. Liens and Collections

1. According to the Eleventh Circuit, the Service is required to make a pre-assessment determination of a taxpayer’s liability as a responsible person under section 6672 when the taxpayer submits a protest, and its failure to do so might render the assessment invalid.

In Romano-Murphy v. Commissioner, the taxpayer served as the chief operating officer of a healthcare staffing business. The Service sent to her a Letter 1153 (notice of proposed assessment) informing her that the Service intended to hold her responsible for a penalty equal to more than $346,000 of the business’s unpaid employment taxes pursuant to section 6672(a). The taxpayer submitted a written protest and requested a conference with IRS Appeals. Due to an unexplained error, the Service never forwarded the protest to IRS Appeals and the taxpayer was not provided with a pre-assessment conference or a final administrative determination as to her protest. Instead, the Service assessed the tax and issued a notice of intent to levy and notice of federal tax lien, in response to which the taxpayer requested a collection due process hearing. During the CDP hearing, the IRS Appeals Office observed that the taxpayer had not had a pre-assessment opportunity to contest her liability and therefore conducted a post-assessment review of the issues the taxpayer had raised in her protest.

Following this review, the Service issued a notice of determination sustaining the proposed collection. The taxpayer sought review in the Tax Court, which sustained the Service’s determination. The taxpayer moved to vacate on the ground that the Service can collect a tax only after a valid assessment, and that the assessment in her case was invalid because the Service had failed to give her a pre-assessment hearing and determination when she filed her timely protest. The Tax Court (Judge Morrison) concluded that, notwithstanding the Service’s failure to make a pre-assessment determination of liability under section 6672(a) in response to the taxpayer’s protest, section 6672 did not prohibit the Service’s assessment. The Tax Court accordingly denied the taxpayer’s motion to vacate.

In an opinion by Judge Jordan, the Court of Appeals for the Eleventh Circuit held that the Service erred in failing to make a pre-assessment determination of the taxpayer’s liability under section 6672(a) in response to her protest. The Eleventh Circuit vacated the Tax Court’s judgment and remanded for a determination whether the Service’s error was harmless or instead rendered the assessment invalid (or required some lesser form of corrective action). In reaching its conclusion that the Service was required to make a pre-assessment determination of liability in response to the taxpayer’s protest, the court relied on several sources of authority. The court first concluded that section 6672(b)(3)—which provides that, “if there is a timely protest of the proposed assessment,” the period of limitations on assessment shall not expire before “the date 30 days after the Secretary makes a final administrative determination with respect to such protest”—contemplates a pre-assessment determination of liability (and notice of such determination to the taxpayer) if a timely protest has been filed. The court therefore rejected the Service’s argument “that it may simply ignore, disregard, or discard a taxpayer’s timely protest to a section 6772(b) pre-assessment notice if it so chooses.”

Assuming for the sake of argument that the language of the statute is ambiguous, the court then reviewed the relevant regulations and concluded that Regulation sections 301.7430-3(d) and 301.6320-1(e)(4) “require the IRS to make a pre-assessment determination (though not necessarily through the provision of a hearing) about a taxpayer’s section 6672(a) liability when timely protest is made.” These Regulations, the court concluded, are entitled to Chevron deference and are binding on the government as well as the taxpayer. Finally, the court regarded Regulation section 601.106(a)(1)(iv) and relevant provisions of the Internal Revenue Manual as persuasive authority that supported its conclusion.

a. On remand, the Tax Court held that the Service’s failure to make a pre-assessment determination of the taxpayer’s liability under section 6672(a) for the trust fund recovery penalty in response to the taxpayer’s protest rendered the assessment invalid and that the error was not harmless. On remand, in a lengthy opinion by Judge Morrison, the Tax Court first concluded that the requirement that the Service make a pre-assessment, final administrative determination about a taxpayer’s section 6672(a) liability when the taxpayer submits a timely protest is a “requirement[] of applicable law or administrative procedure” within the meaning of section 6330(c)(1). Section 6330(c)(1) requires an IRS Appeals officer conducting a collection due process hearing following the Service’s issuance of a final notice of intent to levy to obtain verification “that the requirements of applicable law or administrative procedure have been met.” (By virtue of section 6320(c), this same requirement applies to CDP hearings conducted following the Service’s issuance of a notice of federal tax lien.) In this case, the court observed, the Service had not made the required pre-assessment determination.

The court then held that the Service’s failure to make the required pre-assessment, final administrative determination regarding the taxpayer’s section 6672(a) liability in response to the taxpayer’s protest rendered the assessment invalid. In reaching this conclusion, the court drew an analogy to its prior holdings that the Service’s failure to issue a notice of deficiency when required by section 6213(a) renders a subsequent assessment invalid. Because the assessment was invalid, the court concluded, it was an abuse of discretion for the IRS Appeals officer to uphold the proposed levy and filing of notice of lien to collect the trust fund recovery penalty from the taxpayer. Finally, the court concluded that the Service’s failure to make the required pre-assessment determination of liability was not harmless error. Accordingly, the court declined to sustain the notice of determination issued by IRS Appeals.

2. ♪♫ You say $19.5 million, I say $12,603. Let’s call the whole thing off. ♫♪ We don’t see many taxpayer victories in the Tax Court following a CDP hearing, but this case is one of them.

In Campbell v. Commissioner, in response to a notice of federal tax lien and a final notice of intent to levy with respect to $1.2 million of unpaid tax liability and an accuracy-related penalty for 2001, the taxpayer requested a CDP hearing. Following the CDP hearing, the Service issued a notice of determination upholding the proposed collection action. The taxpayer sought a review of the notice of determination by filing a petition in the Tax Court. In response to motions for summary judgment by the Service, the Tax Court twice remanded the case to the IRS Appeals Office for supplemental CDP hearings. In the first supplemental CDP hearing, the taxpayer submitted a $12,603 offer-in-compromise for all liabilities. The Service calculated the taxpayer’s reasonable collection potential (RCP) as $1.5 million and issued a notice of determination rejecting the proposed offer-in-compromise. The taxpayer asserted that, in the first supplemental CDP hearing, the Service had failed to address state law issues that could affect nominee and alter ego theories. In the second supplemental CDP hearing, the Appeals officer increased the taxpayer’s RCP to $19.5 million, issued a second supplemental notice of determination rejecting the taxpayer’s offer-in-compromise, and sustained the proposed collection action.

The Tax Court (Judge Kerrigan) held that the IRS Appeals officer abused her discretion in upholding the proposed collection action and declined to sustain the notice of determination. Specifically, the court held that the Appeals officer abused her discretion in determining the taxpayer’s RCP in three respects. First, according to the Internal Revenue Manual, dissipated assets can be taken into account in determining a taxpayer’s RCP if the transfer of assets took place within a three-year period immediately preceding the taxpayer’s submission of an offer-in-compromise. Generally, dissipated assets are those assets disposed of in an attempt to avoid payment of a tax liability or those assets disposed of, other than for the production of income or for the health and welfare of the taxpayer and family members, after the tax is assessed. Assets transferred outside the three-year look-back period can be taken into account if they were transferred within six months before or after the tax was assessed. The taxpayer had submitted the offer-in-compromise in March 2014. The tax was assessed on April 19, 2010, which meant that the Appeals officer could look back to assets transferred within six months of that date. The Appeals officer, however, took into account $5 million that the taxpayer had contributed in 2004 to an irrevocable grantor trust established in the West Indies. The court found that, even after making this contribution, the taxpayer’s net worth exceeded any potential tax liability and that the Appeals officer had abused her discretion in treating trust assets as dissipated assets. The court also found that the Appeals officer abused her discretion by treating as dissipated assets investments, made in 2006 through 2010, in residential and commercial real estate in the Gulf Coast region under Go Zone legislation. The investments were lost due to issues such as Chinese drywall in some of the homes and the 2008 subprime mortgage crisis. “There is no indication in the record, and none was demonstrated at trial, that petitioner invested in the Go Zone in an attempt to avoid paying his 2001 tax liability.”

Second, the Appeals officer determined that the West Indies trust was a nominee or alter ego of the taxpayer, and therefore the trust’s assets could be taken into account in determining RCP as amounts collectible from third parties. According to Drye v. United States, this conclusion requires an inquiry into whether the taxpayer has rights in the property under state law and, if so, whether the taxpayer’s rights qualify as property rights under federal tax law. The taxpayer, as a beneficiary of the trust and with limited rights to request distributions or to request the replacement of the trustee, argued that he had no property interest in the trust’s assets. The court found that the Appeals officer had abused her discretion in determining that the trust was the taxpayer’s nominee or alter ego because the Service had produced no evidence that petitioner had a property right in the trust under state law.

Third, the court held that the Appeals officer had abused her discretion in determining that the taxpayer had control over the trust’s assets and that the assets, therefore, could be taken into account in determining RCP as assets available to the taxpayer, but beyond the reach of the government. The court found that the taxpayer did not have control over the trustee and specifically did not control the trustee’s decision to invest in some of the taxpayer’s Gulf Coast real estate projects.

3. ♫♪You can’t hurry love. ♪♫ Or is it a levy you can’t hurry? When it comes to beginning the statute of limitations for a wrongful levy action, a levy is “fixed” when performance is complete and “determinable” if the amount that will be owed to the taxpayer can reasonably be determined, says the Sixth Circuit.

Gold Forever Music, Inc. (Gold Forever), a music publishing company, entered into contracts pursuant to which it was entitled to half of the royalties collected for the sale and performance of works by various artists. Gold Forever contracted with Broadcast Music, Inc. (BMI) and Universal Music Publishing (Universal) who engaged directly in licensing the musicians’ works to others. BMI and Universal collected royalties and remitted the royalties to Gold Forever. Edward Holland, Jr., a Motown artist, was the sole owner of Gold Forever. He was involved in authoring a number of famous songs such as “You Can’t Hurry Love” by the Supremes and Phil Collins.

In 2012, the Service served two notices of levy, one each to BMI and Universal in relation to taxes owed by Holland. The notices of levy required the two companies to remit to the Service amounts they were “already obligated to pay [Gold Forever].” Beginning on October 6, 2016, through the date of the complaint, BMI and Universal remitted amounts to the Service. On December 6, 2017, Gold Forever filed a wrongful levy action for amounts remitted beginning on October 6, 2016. The government moved to dismiss Gold Forever’s wrongful levy suit on the basis that it had been filed after the statute of limitations had run. The district court agreed with the government and granted the motion to dismiss. Gold Forever appealed.

Prior to amendment of the statute by the TCJA, section 6532(c)(1) provided that a wrongful levy action must be brought within nine months from the date of the levy. (As a result of the 2017 amendment, this period is now two years.) With respect to intangible property such as the property involved here, the date of the notice of levy in 2012 is treated as the “date of the levy” for purposes of starting the running of the limitations period for a wrongful levy action. Nevertheless, a levy may be imposed only on obligations that exist at the time of the levy. For example, if a bank account is the subject of a levy, the levy attaches only to the assets of the bank account at the time of the levy. If there is a later deposit to the bank account, the levy does not apply to or reach the later deposit. Importantly, an obligation, such as the obligation to pay royalties here, comes into existence “when the liability of the obligor is fixed and determinable” and this is true even though “the right to receive payment thereof may be deferred until a later date.”

Therefore, the question in the case was whether the 2012 notices of levy applied to royalties received after 2012. That question depended on whether the post-2016 royalties remitted to the Service by BMI and Universal were fixed and determinable in 2012 when the notices of levy were initially issued. Based upon this premise, the court narrowed the issue to whether the obligation to pay future royalties to Gold Forever was sufficiently fixed and determinable such that the 2012 levy attached to the later royalty payments.

In addressing this question, the Court of Appeals for the Sixth Circuit compared the holdings of the Ninth Circuit in Tull v. United States and in United States v. Hemmen. In Tull, the taxpayer engaged an auctioneer to auction the taxpayer’s assets. Thereafter, the auctioneer received a notice of levy seeking the auction proceeds. The issue was whether the future auction proceeds were fixed and determinable at the time of the agreement between the taxpayer and the auctioneer. The Ninth Circuit found that “an obligation to attempt to sell some as yet undetermined amount of property for an as yet undetermined price to as yet undetermined buyers” was not fixed and determinable. In Hemmen, the court held that an administrative claim in a bankruptcy proceeding was fixed and determinable because the underlying performance giving rise to the claim was complete. The court concluded that the mere possibility that the claim might later be disallowed (or defeased) bore no relation as to whether the obligation was determinable.

Following the reasoning in Tull, the court in Gold Forever Music, Inc. ruled that “a contractual obligation to pay money . . . to the taxpayer after the date of the levy is ‘fixed’ where performance is complete and all that remains under the contract is payment . . . to the taxpayer, and ‘determinable’ if, at the time the levy is served, the amount that the taxpayer will be owed can be ascertained with reasonable accuracy, regardless of whether that amount is subject to potential defeasance.” Applying this rule, the court concluded that that post-2016 royalties remitted to the Service were not obligations owed to Gold Forever in 2012. The court reasoned that in 2012, Gold Forever’s agreements with Universal and BMI should have been construed as merely an obligation to attempt to sell some undetermined amount of property for an undetermined price to yet-to-be-determined buyers. The earliest the statute of limitations could have begun running on Gold Forever’s claim was when the Service seized Gold Forever’s funds held by BMI and Universal. Gold Forever’s complaint alleged that it had filed requests for the return of those funds within the requisite nine-month period. Thus, the court held the Service’s notices of levy in 2012 (again treated as the date of the levy) did not apply to any royalties generated after the notices were served and the statute of limitations therefore did not bar Gold Forever’s wrongful levy action.

4. “The Freak” might no longer have a 40-inch vertical leap, but he managed to take down the Service’s notice of federal tax lien following a CDP hearing on the basis that the Appeals officer did not properly verify mailing of the notice of deficiency.

In Kearse v. Commissioner, the taxpayer, Jevon Kearse, who played for more than a decade in the NFL for the Tennessee Titans and the Philadelphia Eagles, took a business bad debt deduction of $1.36 million on his 2010 federal income tax return. The Service disallowed the deduction and assessed tax in the amount of more than $400,000. In response to the Service’s notice of federal tax lien, the taxpayer requested a CDP hearing. In the CDP hearing, the taxpayer submitted an offer-in-compromise based on doubt as to liability and offered to pay $1. He disputed the Service’s proper mailing and his receipt of the statutory notice of deficiency. The IRS Appeals Office issued a notice of determination sustaining the collection action, and the taxpayer sought review by filing a petition in the Tax Court.

Sections 6320(c) and 6330(c) require the Appeals officer conducting the CDP hearing to verify that the requirements of applicable law and administrative procedure were met. In this case, the Appeals officer was unable to secure United States Postal Service Form 3877 to show proof of mailing of the notice of deficiency. She also did not request the statutory notice of deficiency. She instead examined the Service’s Integrated Data Retrieval System (IDRS) to verify that the notice of deficiency was mailed.

The Tax Court (Judge Ashford) held that it was an abuse of discretion for the IRS Appeals officer to sustain the collection action. Before the court, the Service stipulated that the Service was unable to produce USPS Form 3877. The court held that “the Appeals officer failed to properly perform the verification mandated by section 6330(c), i.e., to properly verify that the assessment of petitioner’s unpaid 2010 income tax liability was preceded by a duly mailed notice of deficiency.” Specifically, the court stated:

Where a taxpayer alleges that the notice of deficiency was not properly mailed to him, he has “alleged an irregularity” . . . thereby requiring Appeals officers, according to further IRS guidance, to do more than “rely solely” on IDRS; they must review: (1) a copy of the notice of deficiency and (2) the USPS Form 3877 or equivalent IRS certified mail list bearing a USPS date stamp or the initials of a postal employee . . . . [T]he Appeals officer here acknowledges that she did not secure (and accordingly review) either of these documents before the notice of determination was issued to petitioner.

The court also rejected the Service’s belated production of USPS Form 3877 because the Service had previously stipulated that it could not produce this form.

5. The Tax Court declines jurisdiction in a case in which the notice of federal tax lien was sent to the proper address and received by the taxpayer.

In Atlantic Pacific Management Group, LLC v. Commissioner, the petitioner, Atlantic Pacific Management Group, LLC (Atlantic), failed to file partnership information returns for two consecutive years. The Service filed a notice of federal tax lien, sent a notice of federal tax lien filing to Atlantic, and assessed late-filing penalties for both years. The notice of federal tax lien notified Atlantic of its right to request a CDP hearing. Although the notice was delivered and signed for, Atlantic did not timely request a CDP hearing. When Atlantic submitted a late request for a CDP hearing, the Service closed the case without conducting a CDP (or equivalent) hearing. The Service also did not issue a notice of determination.

In general, under section 6320(a)(3)(B) and (b)(1), after receiving a notice of federal tax lien, a taxpayer has a 30-day period within which to request a CDP hearing with the IRS Office of Appeals, following which IRS Appeals will issue a notice of determination. Once IRS Appeals issues the notice of determination, the taxpayer, pursuant to sections 6320(c) and 6330(d)(1), can seek judicial review by filing a petition with the Tax Court. Notwithstanding that Atlantic had neither timely filed for a CDP hearing nor received a notice of determination, Atlantic filed a petition with the Tax Court asserting that the court should follow its holding in Buffano v. Commissioner.

The Tax Court (Judge Goeke) held that, when jurisdiction is lacking, the court must nevertheless analyze the underlying facts to decide the proper basis for dismissal. Specifically, Atlantic argued that it was deprived of its right to a CDP hearing and that the court should dismiss due to the Service’s failure to issue a valid notice of federal tax lien. The Service, on the other hand, argued that the court should overrule its decision in Buffano and dismiss for lack of jurisdiction because the Service had not issued a notice of determination. The court declined to adopt either of the parties’ arguments, opting instead to “address some discrepancies in caselaw surrounding [the court’s] authority to determine whether statutory requirements were complied with when determining jurisdiction.” In doing so, the court distinguished Buffano. In Buffano, the taxpayer had failed to submit a timely request for a CDP hearing and had failed to show up for an equivalent hearing granted by the Service. The court in Buffano dismissed and invalidated the underlying levy notice because it was not mailed to the appropriate address. The court distinguished the lack of notice to the taxpayer in Buffano from Atlantic’s actual receipt of proper notice. The court concluded that it lacked jurisdiction because no notice of determination was issued.

The court also rejected Atlantic’s argument that section 7803(a)(3), the statutory Taxpayer Bill of Rights (TBOR) enacted as part of the Protecting Americans from Tax Hikes Act (PATH) of 2015, conferred jurisdiction on the court. According to Atlantic, section 7803(a)(3) gave “it a right to be heard and to appeal decisions of respondent to an independent forum.” Unimpressed with this argument, the court held that section 7803(a)(3) provides no independent relief or additional rights to taxpayers and confers no power on the court to extend the deadline for requesting a CDP hearing beyond the 30 days prescribed by section 6320.

The court’s holding regarding the statutory TBOR is consistent with its decision in Moya v. Commissioner, concluding that the TBOR adopted by the Service in 2014 did not add to a taxpayer’s rights but merely “consolidat[ed] and articulat[ed] in 10 easily understood expressions rights enjoyed by taxpayers and found in the Internal Revenue Code and in other IRS guidance” and with the decision in Facebook, Inc. v. Internal Revenue Service, holding that the statutory TBOR of section 7803(a)(3) did not grant taxpayers new enforceable rights.

6. Congress has excluded certain categories of tax debts from the clutches of private debt collectors.

Section 6306 authorizes the Service to enter into “qualified tax collection contracts” with private debt collectors to locate and contact taxpayers, make payment arrangements, and obtain financial information. Nevertheless, section 6306(d) provides that certain tax receivables are not eligible for collection under qualified tax collection contracts, including receivables subject to a pending or active installment agreement or offer-in-compromise, those classified as innocent spouse cases, and those involving a taxpayer identified as being deceased or under the age of 18.

Section 1205 of the Taxpayer First Act amends section 6306(d)(3) to add two new categories of receivables that are excluded from qualified tax collection contracts. New section 6306(d)(3)(D) excludes tax receivables involving a taxpayer substantially all of whose income consists of Social Security disability insurance benefits or supplemental security income benefits, and new section 6306(d)(3)(E) excludes tax receivables involving a taxpayer whose adjusted gross income (for the most recent taxable year for which information is available) does not exceed 200% of the applicable poverty level. These amendments apply to tax receivables identified by the Service after December 31, 2020.

7. Congress has codified the waiver of fees for low-income taxpayers submitting an offer-in-compromise.

Generally, under section 7122(c)(1)(A), a taxpayer making a lump-sum offer-in-compromise must submit with the offer a payment of 20% of the amount offered. A taxpayer also must pay a user fee (currently $186) for processing the offer-in-compromise. Through administrative guidance, the up-front partial payment and the user fee are waived for low-income taxpayers.

Section 1102 of the Taxpayer First Act amends section 7122(c) by adding new section 7122(c)(3), which codifies these waivers. Section 7122(c)(3) provides that the up-front partial payment and user fee do not apply to an offer-in-compromise submitted by a taxpayer whose adjusted gross income, for the most recent taxable year for which adjusted gross income is available, does not exceed 250% of the applicable poverty level. This change applies to offers-in-compromise submitted after July 1, 2019, the date of enactment.

G. Innocent Spouse

1. Even a Johnny Cash song couldn’t have told a story like this. A taxpayer prevails in her quest for innocent spouse relief.

In Contreras v. Commissioner, the taxpayer sought innocent spouse relief under section 6015(f) with respect to the years 2006 through 2009. The taxpayer married her husband in August of 2000. He had his own home construction business, and she stayed home to care for their two children and her husband’s two children from a prior relationship. They lived in a mobile home on an undeveloped lot, Lot 12, in Liberty County, Texas, and they planned to build a home on the lot next door, Lot 13. When they applied for financing to assist with construction, the taxpayer learned that Lot 13 was owned by her husband and the woman with whom he was previously in a relationship. She and her husband were advised by an attorney that her husband was still in a common-law marriage with the other woman and that, to remove the other woman’s name from the title to Lot 13, her husband would have to go through a divorce proceeding, which he did. This necessarily meant that when the taxpayer had married her husband, he was already married, and therefore the taxpayer was never legally married to him. Ultimately, her husband built the house on Lot 13, largely using materials left over from various jobs of his home construction business, and the family moved into the home.

During the course of their relationship, the taxpayer’s husband was abusive and routinely came home in a drunken state. The police were called to their home on several occasions, they argued, he kicked in a bedroom door, damaged property, threw the taxpayer’s possessions outside the home, and committed other aggressive acts. On these occasions, the taxpayer often left their home with her children to go to the home of her grandmother. The taxpayer’s husband had at least one affair with another woman during their marriage. Her husband handled the filing of their federal income tax returns. No returns were filed for the year 2006 through 2009.

The taxpayer divorced her husband in 2011. Just prior to their divorce, the Service filed a notice of lien against her husband and, just after the divorce, the Department of Justice brought an action in federal district court seeking to reduce tax liabilities to judgment and to foreclose on the home on Lot 13, where the taxpayer lived with her two children following the divorce. The decree of divorce awarded each spouse as separate property a one-half interest in Lots 12 and 13. In addition, the divorce decree awarded the taxpayer $127,050 and authorized the taxpayer to foreclose on her ex-husband’s interest in Lots 12 and 13 if he did not pay this amount by a specified date. Her ex-husband failed to pay this amount and voluntarily transferred to the taxpayer his interests in Lots 12 and 13. The deed transferring title was prepared with the assistance of an attorney and recorded in the public land records.

Following their divorce, the taxpayer’s ex-husband filed returns for 2008 and 2009 with the incorrect filing status of head of household. In 2013, in connection with an audit of the years 2006 through 2009, the taxpayer signed joint returns for 2006 and 2007 as well as amended joint returns for 2008 and 2009. She placed the words “as to form” next to her signature on the 2006 and 2007 returns. She repeatedly expressed that she did not understand the returns and did not understand why she had to sign a joint return with her ex-husband. She was represented in the course of the audit by an attorney whose fees were paid by her ex-husband. The Service sought to hold the taxpayer liable for nearly $300,000 in taxes, penalties, and interest for the years 2006 through 2009. The taxpayer filed an administrative request for innocent spouse relief, which the Service denied. The taxpayer then filed a petition in the Tax Court.

The Tax Court (Judge Paris) held that the taxpayer was entitled to innocent spouse relief under section 6015(f) (equitable relief) with respect to all of the years at issue. The taxpayer and the Service agreed that the taxpayer met all threshold requirements for equitable relief under Revenue Procedure 2013-34, except for one. The Service asserted that assets, the two undeveloped lots, were transferred between the spouses as part of a fraudulent scheme. The court rejected this argument largely on the basis that the transfer was made pursuant to rights granted to the taxpayer in the divorce decree and that the taxpayer and her husband had not attempted to conceal the transfer; they had recorded the transfer in the public land records.

The court also rejected the Service’s arguments that the taxpayer was not entitled to streamlined relief under Revenue Procedure 2013-34. The Service argued that the taxpayer would not suffer economic hardship if relief were not granted, which the court rejected on the basis that the taxpayer’s only sources of income were unreliable child support payments and government assistance. The Service also argued that streamlined relief was unavailable because the taxpayer had knowledge that her ex-husband would not or could not pay the liabilities in question. The court rejected this argument based on the taxpayer’s credible testimony, as well as that of her daughter, regarding her ex-husband’s abusive and controlling behavior.

2. Congress has clarified the scope and standard of review in the Tax Court of determinations with respect to innocent spouse relief and has specified limitations periods for seeking equitable innocent spouse relief under section 6015(f).

Section 1203 of the Taxpayer First Act amends section 6015(a) to clarify the scope and standard of review in the Tax Court of any determination with respect to a claim for innocent spouse relief, i.e., any claim for relief under section 6015 from joint and several liability for tax liability arising from a joint return. Pursuant to the amendment, the Tax Court’s scope of review is based on the administrative record and “any additional newly discovered or previously unavailable evidence.” The standard of review in the Tax Court is de novo.

This amendment is consistent with the Tax Court’s holding in Porter v. Commissioner, but resolves conflicting decisions on this issue in cases in which the taxpayer sought equitable innocent spouse relief under section 6015(f), some of which had held that the Tax Court’s review is limited to the administrative record and that the Tax Court’s standard of review is abuse of discretion.

The legislation also amends section 6015(f) by adding new section 6015(f)(2), which specifies the time within which a taxpayer can assert a claim for equitable innocent spouse relief under section 6015(f). With respect to any unpaid tax, a taxpayer can assert such a claim within the limitations period provided in section 6502 on collection of tax (generally within ten years after assessment). With respect to any tax that has been paid, the taxpayer can assert a claim for equitable innocent spouse relief within the period within which the taxpayer could have submitted a timely claim for refund. Generally, this period is set forth in section 6511(a)–(b).

Each of these amendments applies to petitions or requests for innocent spouse relief filed or pending on or after July 1, 2019, the date of enactment.

H. Miscellaneous

1. The Tax Court trashes the Service’s understanding of what’s a legislative regulation and what’s an interpretive regulation and thus requires tax lawyers to learn all the APA stuff that other administrative law lawyers have to know.

In a reviewed, unanimous opinion by Judge Marvel in Altera Corp. v. Commissioner, the Tax Court invalidated regulations under section 482 (Regulation section 1.482-7(d)(2)) requiring participants in qualified cost-sharing arrangements to include stock-based compensation costs in the cost pool in order to comply with the arm’s length standard. These Regulations overturned the Tax Court’s earlier decision in Xilinx Inc. v. Commissioner, holding that, under the 1995 cost-sharing regulations, controlled entities entering into qualified cost-sharing agreements need not share stock-based compensation costs because parties operating at arm’s length would not do so. In Altera Corp., the court found that the Regulations were not the product of reasoned decision making as required by section 706(2)(A) of the Administrative Procedure Act and the Supreme Court’s decision in Motor Vehicle Manufacturers Association of the United States v. State Farm Mutual Automobile Insurance Co.

According to Professor Kristin Hickman, “From top to bottom, the Altera opinion reads like a treatise on general administrative law requirements and norms.” The Tax Court’s opinion has a number of potential implications, which Professor Hickman has summarized as follows.

Since the Supreme Court decided the Mayo Foundation case in 2011 [Mayo Foundation for Medical Research v. United States, 562 U.S. 44 (2011)], the government has done everything it can to limit the scope of the Supreme Court’s 2011 Mayo Foundation decision. Even though the Mayo Foundation Court declined “to carve out an approach to administrative review good for tax law only” and otherwise signaled fealty to general administrative law norms in the tax context, the IRS and the Department of Justice have repeatedly pursued a narrow construction of Mayo Foundation, and the Tax Court has often been happy to play along. Not today. . . .

First, notwithstanding the Supreme Court’s conclusion in Mayo Foundation that general authority Treasury regulations issued under Section 7805(a) carry the force of law, in the Internal Revenue Manual and elsewhere, the IRS has continued to assert that most of its regulations are interpretative rules exempt from APA notice-and-comment procedural requirements. Applying the Ninth Circuit’s version of the American Mining Congress [v. Mine Safety & Health Admin., 995 F.2d 1106, 1109 (D.C. Cir. 1993)] standard for distinguishing between legislative regulations that require notice-and-comment rulemaking and interpretative regulations that do not [see Hemp Indus. Ass’n v. DEA, 333 F.3d 1082, 1087 (9th Cir. 2003) (stating that, in general terms, interpretive rules merely explain preexisting substantive law while legislative rules “create rights, impose obligations, or effect a change in existing law”)], the Tax Court held that the Treasury regulation at issue in Altera was a legislative rule because the regulation was necessary to sustain an adjustment to the taxpayer’s income and because Treasury expressly invoked general rulemaking authority under Section 7805(a) in promulgating the regulation. In reaching that decision, moreover, the Tax Court also concluded more broadly that regulations promulgated pursuant to Section 7805(a) “carry the force of law” and that “the Code imposes penalties for failing to follow them,” such that “‘Congress has delegated legislative power to’ Treasury” through that grant of general rulemaking authority—i.e., making regulations promulgated under that authority legislative rules subject to notice-and-comment rulemaking requirements. Elsewhere in the opinion, the Tax Court acknowledged that its past practice of referring “to regulations issued pursuant to specific grants of rulemaking authority as legislative regulations and regulations issued pursuant to Treasury’s general rulemaking authority, under sec. 7805(a), as interpretive regulations” was inconsistent with general administrative law use of the legislative and interpretive labels.

Second, notwithstanding the Supreme Court’s refusal in Mayo Foundation to approach judicial review in general (rather than merely Chevron[, U.S.A., Inc. v. Natural Res. Def. Council, Inc., 467 U.S. 837 (1984)] review) differently in tax cases, the IRS in Altera resisted the taxpayer’s argument that the regulation in question had to satisfy the reasoned decision making requirements of APA § 706(2)(A) and State Farm. The IRS claimed that Chevron, rather than State Farm, provided the appropriate evaluative standard. The precise relationship between Chevron and State Farm standards is unclear, with some courts and scholars contending that they overlap considerably, and others maintaining they are conceptually distinct. Regardless, courts and scholars generally would agree that agency regulations must satisfy both Chevron’s demand that they be substantively reasonable and State Farm’s requirement that they be the product of reasoned decisionmaking. Consistent with some appellate court decisions and a bit of dicta from the Supreme Court in Judulang v. Holder, 132 S. Ct. 476, 483 n.7 (2011), the Tax Court collapsed the two standards, reasoning that “the final rule must satisfy State Farm’s reasoned decisionmaking standard” because, even if Chevron provided the appropriate evaluative standard, State Farm’s analysis is part of Chevron step two. State Farm analysis is very case by case, requiring both specific allegations as to where the agency’s contemporaneous justification of its decisions is lacking and careful examination of the administrative record to support those allegations. Consequently, State Farm analysis is at least somewhat dependent upon interested parties raising issues and endeavoring to engage the agency in the rulemaking process itself. Commentators did so here. And examining the rulemaking record meticulously and at some length, the Altera court concluded that Treasury and the IRS simply failed to satisfy State Farm’s reasoned decisionmaking requirements. In particular, the court noted that Treasury’s assumptions in adopting the rule were unsupported by evidence regarding real-world practices; that commentators introduced “significant evidence” in the rulemaking process that contradicted Treasury’s assumptions; and that Treasury failed to respond to much of that evidence.

Finally, the Tax Court rejected the government’s claim that deficiencies in Treasury’s reasoning represented harmless error for purposes of APA § 706. According to the court, it was not clear from the administrative record that Treasury would have adopted the same regulation had Treasury determined the inclusion of stock-based compensation costs in the cost pool to be inconsistent with the arm’s length standard.

Altera represents a natural extension of the Supreme Court’s reasoning in the Mayo Foundation case, reflecting the spirit of that decision’s rejection of tax exceptionalism from general administrative law requirements, doctrines, and norms. Given the Altera court’s reasoning, it is difficult to imagine the IRS being able to argue successfully ever again that any Treasury regulation—whether promulgated under specific or general authority—is exempt from APA notice-and-comment rulemaking requirements as an interpretative rule. The Altera court’s analysis therefore removes a layer of uncertainty risk for attorneys seeking to challenge Treasury regulations on APA grounds. Separately, as Pat Smith has documented [Patrick J. Smith, The APA’s Arbitrary and Capricious Standard and IRS Regulations, 136 Tax Notes 271 (July 16, 2012)], many IRS regulations lack the sort of extensive contemporaneous justification of IRS policy choices that State Farm requires, and thus are susceptible to taxpayer claims that they fail to satisfy State Farm’s reasoned decisionmaking standard. Taken comprehensively, the Altera litigation is an exemplar for attorneys seeking to challenge other Treasury regulations under APA § 706(2)(A) and State Farm.

Whether and to what extent the Tax Court will extend general administrative law doctrines beyond Treasury regulations to other IRS actions remains to be seen. For example, some Tax Court judges have been reluctant to extend State Farm analysis to deficiency notices and other IRS determinations respecting individual taxpayers, accepting IRS claims that Mayo Foundation applies only to Treasury and IRS rulemaking and not to IRS adjudications (even though Judulang v. Holder involved an agency adjudication).

Regardless, the fact that the Tax Court unanimously backed such a thorough and unequivocal application of general administrative law principles in reviewing a Treasury regulation is truly remarkable. The Tax Court’s decision in Altera should send a very powerful message to Treasury and the IRS that they need to be more attentive to administrative law requirements in promulgating tax regulations.

a. The Tax Court got it wrong, says the Ninth Circuit. The Regulations at issue are entitled to Chevron deference and were not arbitrary and capricious under the Administrative Procedure Act. In an opinion by Judge Thomas, the Court of Appeals for the Ninth Circuit has reversed the Tax Court and held that Regulation section 1.482-7(d)(2) is valid. The Regulation requires related business entities to share the cost of employee stock compensation in order for their cost-sharing arrangements to be classified as qualified cost-sharing arrangements. In essence, the taxpayer’s primary challenge to the Regulation was that taking stock-based compensation into account in the manner required is inconsistent with the arm’s length standard under section 482 without evidence that parties acting at arm’s length take stock-based compensation into account in similar circumstances.

In reaching its conclusion, the Ninth Circuit first assessed the validity of the Regulation by applying the two-step Chevron analysis. The court concluded in Chevron step one that the statute, section 482, is ambiguous, and in step two that Regulation section 1.482-7(d)(2) is a permissible construction of the statute. In its analysis of Chevron step one, the court examined not only the plain language of the statute but also its legislative history. The court then examined whether the procedures that the Treasury Department used in issuing the Regulation complied with the Administrative Procedure Act. The court rejected the taxpayer’s argument that the regulation was arbitrary and capricious under Motor Vehicle Manufacturers Ass’n of the United States, Inc. v. State Farm Mutual Automobile Insurance Co. The standard in State Farm requires the agency issuing the regulation to “examine the relevant data and articulate a satisfactory explanation for its action including a ‘rational connection between the facts found and the choice made.’” According to the Ninth Circuit, the Regulation in question satisfied this standard:

Thus, the 2003 regulations are not arbitrary and capricious under the standard of review imposed by the APA. Treasury’s regulatory path may be reasonably discerned. Treasury understood section 482 to authorize it to employ a purely internal, commensurate with income approach in dealing with related companies. It provided adequate notice of its intent and adequately considered the objections. Its conclusion that stock-based compensation should be treated as a cost was adequately supported in the record, and its position did not represent a policy change under [FCC v. Fox Television Stations, Inc., 556 U.S. 502, 513 (2009)].

2. No, you can’t plead the Fifth Amendment to avoid a deficiency assessment under section 280E and, duh, when your company’s name is “THC, LLC,” the Service probably is going to figure out that you sell marijuana.

Feinberg v. Commissioner, involved weird facts: an LLC aptly but perhaps stupidly named Total Health Concepts, LLC (THC) had elected Subchapter S status. The case also had procedural quirks: the Service agreed with the taxpayers (the members of THC) that the Tax Court’s reasoning for upholding an asserted deficiency due to the failure to substantiate expenses should be overturned.

The Tax Court had upheld the deficiency based upon the taxpayers’ failure to substantiate expenses. On appeal, the Court of Appeals for the Tenth Circuit (Judge McHugh) ruled that this was improper because the notice of deficiency itself did not raise the issue of substantiation. Nevertheless, the Tenth Circuit upheld the Tax Court’s ultimate conclusion on the basis of section 280E. Section 280E disallows any deduction or credit otherwise allowable if such amount is paid or incurred in connection with a “trade or business (or the activities which comprise such trade or business) [that] consists of trafficking in controlled substances.” The notice of deficiency asserted that the taxpayers’ LLC-S corporation, THC, was unlawfully trafficking in a controlled substance.

A Service notice of deficiency generally is presumed correct unless the taxpayer offers contrary evidence. The Tenth Circuit agreed with the Service that section 280E disallowed the taxpayers’ deductions because the taxpayers had not met their burden of proof when they failed to offer any evidence contrary to the notice of deficiency. Because the deficiency was based on the Service’s disallowance of deductions under section 280E and because the taxpayers had failed to provide any evidence that it was not in the marijuana business, the Service’s position was upheld.

The Tenth Circuit also rejected the taxpayers’ argument that placing the burden of proof on them violated their Fifth Amendment privileges against self-incrimination. The court held that, although the Fifth Amendment provides protection against self-incrimination in criminal proceedings, it does not shift the burden of proof to the Service in a civil tax matter.

3. The D.C. Circuit reversed a federal district court and held that the Service can charge fees for issuing PTINs.

In Montrois v. United States, a group of tax return preparers filed a class-action lawsuit in federal district court challenging the Service’s practice of charging a fee for issuing preparer tax identification numbers (PTINs). The tax return preparers argued that the Service lacked authority under the Independent Offices Appropriations Act to charge a fee for issuing and renewing PTINs and that the Service’s decision to charge fees was arbitrary and capricious in violation of the Administrative Procedure Act. The district court held that, although the Service had statutory authority to require the use of PTINs by those who prepare tax returns for compensation, it lacked legal authority to charge fees for issuing PTINs. The court declared all fees charged by the Service for issuing PTINs unlawful, permanently enjoined the United States from charging such fees, and ordered the United States to refund all PTIN fees paid from September 1, 2010 to the present.

The government appealed the district court’s decision to the Court of Appeals for the District of Columbia Circuit. In an opinion by Judge Srinivasan, the D.C. Circuit reversed the district court’s decision. As discussed in more detail below, the court held that the Service acted within its authority under the Independent Offices Appropriations Act in charging tax return preparers a fee to obtain and renew PTINs, and the court also concluded that the Service’s decision to charge a fee was not arbitrary and capricious. The court remanded the case to the district court for further proceedings, including a determination of whether the amount of the PTIN fee unreasonably exceeds the costs to the Service to issue and maintain PTINs.

a. The Independent Offices Appropriations Act provides the Service with legal authority to charge a fee for issuing PTINs. The D.C. Circuit reviewed its own prior decisions and those of the Supreme Court and, based on this review, reasoned that the Independent Offices Appropriations Act does not authorize federal agencies to tax, which is a legislative power, but rather to impose reasonable fees for benefits conferred on identifiable beneficiaries. According to the court, “[t]o justify a fee under the [Independent Offices Appropriations] Act, then, an agency must show (i) that it provides some kind of service in exchange for the fee, (ii) that the service yields a specific benefit, and (iii) that the benefit is conferred upon identifiable individuals.” The Service, the court concluded, had met these requirements with respect to the fee charged for issuing a PTIN. The function provided by the Service is the issuance of the PTIN, a unique identifying number for each tax return preparer, and the maintenance of the database of PTINs, which enables preparers to use those numbers in place of their Social Security numbers on tax returns. This service yields a specific benefit, the court concluded, because it protects a tax return preparer’s identity by allowing the preparer to list the PTIN on returns rather than the preparer’s social security number. The court also determined that this benefit is conferred upon identifiable individuals because tax return preparers qualify as identifiable recipients for this purpose. Although practically anyone can obtain a PTIN, the benefit of PTINs is conferred upon identifiable individuals (those who apply for them), just as the benefit of the State Department’s fee for issuing a passport is conferred upon identifiable individuals (those who apply for passports).

b. The Service’s decision to charge a fee for issuing PTINs was not arbitrary and capricious. Under section 706(2)(A) of the Administrative Procedure Act, an agency’s decision must be the product of reasoned decision making. The tax return preparers challenging the PTIN fees argued that this requirement was not met because the 2010 regulations that originally established the PTIN fee stated that the fee would pay for the registered tax return preparer program, which was ruled invalid in Loving v. Internal Revenue Service. The D.C. Circuit held, however, that the Service had given adequate reasons for its decision to impose a fee independent of those rejected in Loving. Specifically, the court stated, “[w]hen the IRS reissued the PTIN fee regulations after Loving, it explained that PTINs would benefit preparers by protecting their confidential information and would improve tax compliance and administration.”

On May 24, 2019, the tax return preparers who challenged the Service’s ability to charge fees for issuing PTINs filed a petition for a writ of certiorari with the Supreme Court. The Court declined to review the decision of the D.C. Circuit.

4. Another lesson on mailing a petition to the Tax Court: the date printed on a postage label purchased through the internet will be disregarded if the envelope also bears a U.S. Postal Service postmark.

In Jordan v. Commissioner, the last day for the taxpayer to file a Tax Court petition was March 6, 2018. The taxpayer, who represented herself, printed a label from Endicia.com, an online postage provider, dated March 6, 2018. The envelope containing the petition also bore two U.S. Postal Service postmarks dated March 7 and March 20, 2018. The Tax Court received and filed the petition on March 26, 2018, which was 20 days after the date shown on the Endicia.com label. The Tax Court (Judge Buch) dismissed the petition as untimely filed by relying on Regulation section 301.7502-1(c)(1)(iii)(B)(3), which provides:

If the envelope has a postmark made by the U.S. Postal Service in addition to a postmark not so made, the postmark that was not made by the U.S. Postal Service is disregarded, and whether the envelope was mailed in accordance with this paragraph (c)(1)(iii)(B) will be determined solely by applying the rule of paragraph (c)(1)(iii)(A) of this section [regarding envelopes nearing U.S. postmarks].

The court noted that, in Pearson v. Commissioner, a majority of the court held that internet-purchased postage may qualify as a postmark not made by the U.S. Postal Service under section 7502(b). Because the envelope with the taxpayer’s petition bore a private postmark of March 6, 2018, and later U.S. Postal Service postmarks, the court gave effect to the U.S. Postal Service postmarks. Because both of the U.S. Postal Service postmarks were dated after the last day of the 90-day period for filing a petition with the Tax Court, the court granted the government’s motion to dismiss for lack of jurisdiction.

The court further held that, even if it were to give effect to the March 6 date of the private postmark, it would still have to dismiss for lack of jurisdiction because, under Regulation section 301.7502-1(c)(1)(iii)(B)(1)(ii), in order to treat the date on a private postmark as the date of mailing for purposes of the timely-mailed-is-timely-filed rule, the item must be received by the relevant agency no later than the time when a properly addressed and mailed envelope sent by the same class of mail would ordinarily be received if it were postmarked at the same point of origin by the U.S. Postal Service. In this case, the court noted, “[a]ccording to USPS delivery standards, an item sent by First Class mail from Detroit should arrive in Washington, D.C., in three days,” but the taxpayer’s petition had arrived 20 days after the date of the private postmark.

5. A federal district court concluded that Form 1099-A issued by a mortgage lender showed only that the lender had acquired the property serving as security for the loan, not that the loan was canceled, which would have been reported on form 1099-C, and therefore dismissed the borrower’s claim that the lender caused him to owe more tax than he properly owed.

In Helmert v. Cenlar FSB, John Helmert, Jr., and his former wife financed the purchase of their home and executed a deed of trust in favor of the lender. They later refinanced their home loan with a different lender and executed a deed of trust in favor of the new lender. The new deed of trust ultimately was assigned to a lender that conducted a foreclosure sale. Mr. Helmert brought an action in which he asserted various claims against the lenders involved, including a claim for wrongful foreclosure. One of the claims he asserted was that the lender that foreclosed improperly issued two Forms 1099-A that caused his tax liability to be greater than the amount he actually owed. The lenders against whom the action was brought moved to dismiss his claims.

The district court (Judge Mills) dismissed some of Mr. Helmert’s claims, including his claim that the lender’s improper issuance of the Forms 1099-A had increased his tax liability. Mr. Helmert asserted that Form 1099-A is issued to reflect loan forgiveness. The court explained that Form 1099-C, not Form 1099-A, is issued to reflect the cancellation of debt. Form 1099-A, the court stated, “merely shows that the lender has acquired the property serving as security for its loan, while also stating the balance owed and the fair market value of the property.” Because Mr. Helmert had not submitted Form 1099-C or his individual income tax return to support his claim that the lender had caused him to have an increased tax liability, the court dismissed his claim.

The instructions to Form 1099-A discuss the coordination of Forms 1099-A and 1099-C. The instructions state:

If, in the same calendar year, you cancel a debt of $600 or more in connection with a foreclosure or abandonment of secured property, it is not necessary to file both Form 1099-A and Form 1099-C, Cancellation of Debt, for the same debtor. You may file Form 1099-C only. You will meet your Form 1099-A filing requirement for the debtor by completing boxes 4, 5, and 7 on Form 1099-C. However, if you file both Forms 1099-A and 1099-C, do not complete boxes 4, 5, and 7 on Form 1099-C.

6. The Service expands the voluntary IP PIN program to a total of nine states and the District of Columbia.

An Identity Protection Personal Identification Number (IP PIN) is a six-digit number assigned to eligible individuals that must be used on a tax return, in addition to the individual’s Social Security number (SSN), to verify the individual’s identity. The IP PIN helps prevent a taxpayer’s SSN from being used on a fraudulent federal income tax return. The Service assigns an IP PIN to taxpayers who are victims, or suspected victims, of identity theft.

For the 2016 filing season, the Service implemented a pilot program under which taxpayers who filed returns during the prior year and reside in the District of Columbia, Florida, and Georgia are eligible to obtain an IP PIN on a voluntary basis even though they have not experienced identity theft. For the 2019 filing season, the Service expanded this program to include California, Delaware, Illinois, Maryland, Michigan, Nevada, and Rhode Island. The Service selected these nine states and the District of Columbia because they have higher levels of identity theft. Taxpayers who filed returns from these jurisdictions in the prior year can obtain an IP PIN by using the Service’s “Get An IP PIN Tool.” To obtain an IP PIN, taxpayers will need to successfully complete the Service’s identity verification secure access process. If its systems can handle the expansion, the Service plans to eventually offer the voluntary IP PIN program to taxpayers in all states, a move that is supported by the AICPA.

a. Congress has required annual expansion of the voluntary IP PIN program each year and full implementation within five years. Section 2005 of the Taxpayer First Act directs the Secretary of the Treasury or the Secretary’s delegate to establish a program to issue an IP PIN to any individual residing in the United States who requests one to assist the Secretary in verifying the individual’s identity. For each calendar year beginning after July 1, 2019 (the date of enactment), the legislation requires the Secretary to provide IP PINs to individuals residing in such states as the Secretary deems appropriate, provided that the total number of states served by the program increases each year. The legislation also requires that the program be available to all individuals within the United States not later than five years after the date of enactment.

7. The Service releases final Regulations permitting the use of truncated taxpayer identification numbers on Forms W-2 furnished to employees.

Final Regulations, adopted without substantive change from the Proposed Regulations issued in 2017 under sections 6051, 6052, and 6109, permit employers voluntarily truncation of employees’ social security numbers (SSNs) on copies of Forms W-2 that are furnished to employees (including Forms W-2 reporting payment of wages in the form of group-term life insurance) so that the truncated SSNs appear in the form of Service truncated taxpayer identification numbers (TTINs). Employers are not permitted to truncate SSNs on Forms W-2 filed with the Service or with the Social Security Administration. Similarly, TTINs may not be used on statements furnished to employers of a payee who received sick pay (such as a statement furnished to the employer of an employee by an insurance company making payments to an employee who is temporarily absent from work due to sickness or disability). According to Regulation section 301.6109-4(a), a TTIN

is an individual’s social security number (SSN), IRS individual taxpayer identification number (ITIN), IRS adoption taxpayer identification number (ATIN), or IRS employer identification number (EIN) in which the first five digits of the nine-digit number are replaced with Xs or asterisks. The TTIN takes the same format of the identifying number it replaces, for example XXX-XX-1234 when replacing an SSN, or XX-XXX1234 when replacing an EIN.

The final Regulations apply to returns, statements, and other documents required to be filed or furnished after December 31, 2020, except for the rules regarding information returns filed with the Social Security Administration, which apply as of July 3, 2019.

8. Even if the Service violated certain rights enumerated in the TBOR adopted by the Service, the violations do not provide a basis for invalidating a notice of deficiency issued to the taxpayer.

In Moya v. Commissioner, the Service disallowed deductions the taxpayer had claimed with respect to business activity on Schedule C of her 2011, 2012, and 2013 federal income tax returns. During those years, she was a professor at the College of Southern Nevada. She subsequently moved to Santa Cruz, California. The Service’s examination of the taxpayer’s returns was conducted by the Service office in Las Vegas, Nevada. Through written correspondence, the taxpayer requested that the examination of her returns be transferred to a Service office near her home in Santa Cruz and that a hearing, scheduled for Las Vegas, also be relocated to Santa Cruz. The Service subsequently issued a notice of deficiency in which it disallowed the taxpayer’s deductions on Schedule C.

The taxpayer filed a petition in the Tax Court. In the petition, the taxpayer gave the following reasons for challenging the proposed disallowance:

Although she requested that the examination of her returns be set near her home, in Santa Cruz, it was set in Las Vegas; her phone calls to the IRS went unreturned; she received contradictory information as to where the examination of her returns would take place; and she received inconsistent requests for information.

The taxpayer asserted that the TBOR, adopted by the Service in 2014, gave her the right to have her questions answered and to meet with a Service representative at a time and place convenient to her, and that she was afforded neither right. The taxpayer’s position was that, in examining her returns, the Service had violated her rights to be informed, to challenge the Service’s position and be heard, and to a fair and just tax system. The Service argued that pursuant to the principle set forth in Greenberg’s Express, Inc. v. Commissioner, a proceeding in the Tax Court to redetermine a deficiency is a proceeding de novo, and therefore the Tax Court generally is precluded from looking behind a notice of deficiency to examine the Service’s policy or procedures in making determinations.

The Tax Court (Judge Halpern) ruled in favor of the Service for two reasons. First, the court explained, the TBOR adopted by the Service did not add to her rights. The court traced the history of the TBOR and concluded that it merely “consolidat[ed] and articulat[ed] in 10 easily understood expressions rights enjoyed by taxpayers and found in the Internal Revenue Code and in other IRS guidance.” Second, the court reasoned that, even if true, the taxpayer’s claims did not provide a basis for invalidating the notice of deficiency because the taxpayer had a full opportunity to challenge the Service’s proposed adjustments in the Tax Court. Instead of taking advantage of this opportunity, the court stated, the taxpayer had instead challenged the Service’s right to make those determinations on the basis that it had violated unspecific statutory rights.

In section 401(a) of the Protecting Americans from Tax Hikes (PATH) Act of 2015, Congress amended section 7803(a)(3), which provides that, “[i]n discharging his duties, the Commissioner shall ensure that employees of the Internal Revenue Service are familiar with and act in accord with taxpayer rights as afforded by other provisions of this title, including” ten specific rights. These include “the right to be informed” and “the right to a fair and just tax system.” In Facebook, Inc. v. Internal Revenue Service, the court held that the statutory TBOR in section 7803(a)(3) did not grant taxpayers new, enforceable rights. In Atlantic Pacific Management Group, LLC v. Commissioner, the Tax Court held that section 7803(a)(3) provides no independent relief or additional rights to taxpayers and confers no power on the court to extend the deadline for requesting a CDP hearing beyond the 30 days prescribed by section 6320.

9. When the Service fails to review all evidence related to a whistleblower award, the Tax Court may grant the Service’s motion to remand the case back to the Service to conserve the court’s resources.

In Whistleblower 769-16W v. Commissioner, the petitioner initially applied for seven separate whistleblower awards pursuant to section 7623 in relation to a tax-avoidance scheme allegedly perpetrated by various taxpayers. In late 2011, after referring the petitioner’s claims to the IRS’s Large Business and International (LB&I) Division, LB&I concluded that when the claims for award were submitted, the Service was aware of the tax-avoidance scheme and each of the reported taxpayers was already under examination. Over the course of the same general time period, the petitioner provided a congressional committee responsible for investigations with similar information regarding the tax-avoidance scheme in relation to the same taxpayers. The petitioner later applied for additional whistleblower awards in relation to additional taxpayers.

In 2014 (date unclear), the congressional committee issued its report regarding the tax-avoidance scheme to the Service. Thereafter, the IRS Whistleblower Office issued a final determination summarily denying all of petitioner’s claims indicating the information provided by petitioner did not result in any action or change in position taken by the Service. On appeal to the Tax Court, the petitioner objected to, among other things, the Service’s motion to remand the case back to the Service because, as conceded by the Service, the Whistleblower Office had not considered whether the Service might have proceeded on the basis of information the petitioner brought to the Service’s attention as part of the congressional committee report.

In a unanimous, reviewed opinion by Judge Thornton in a case of first impression, the Tax Court granted the Service’s motion to remand the case to the Service. Remanding to the Service is appropriate, the court held, when the Service identifies substantial concerns related to its ruling and where the remand will conserve the court’s resources. The court cautioned that remand will be granted only if the petitioner will not be unduly prejudiced.

In coming to these conclusions, the court relied on its recent decision in Kasper v. Commissioner, in which the court held that its standard of review in a whistleblower case is for abuse of discretion. In Kasper, the court also noted that it examines requests for innocent spouse relief under section 6015 under a de novo standard of review. In contrast, the court’s standard of review is for abuse of discretion in both collection due process (CDP) cases and whistleblower cases. Thus, while the court may remand a CDP case for abuse of discretion, cases arising under section 6015 are reviewed de novo and are not subject to remand. Cases in the latter category are reviewed de novo because a petition under section 6015 “is generally not a ‘review’ of the Commissioner’s determination in a hearing but is instead an action begun in this Court.” Again citing its decision in Kasper, the court further held that, in reviewing whistleblower award determinations for abuse of discretion, the court will not substitute its judgment for that of the Whistleblower Office. Instead, the court decides “whether the agency’s decision was ‘based on an erroneous view of the law or a clearly erroneous assessment of the facts.’” The court then adopted the standard set forth by the Supreme Court in Camp v. Pitts, for remanding a case to an administrative agency as follows:

If the record before the agency does not support the agency action, if the agency has not considered all relevant factors, or if the reviewing court simply cannot evaluate the challenged agency on the basis of the record before it, the proper course, except in rare circumstances, is to remand to the agency for additional investigation or explanation.

Thus, under Camp, the Tax Court may now remand cases to the Whistleblower Office for further consideration.

Because any appeal of this case will be considered by the Court of Appeals for the District of Columbia Circuit, the court turned to Utility Solid Waste Activities Group v. EPA to explain the manner in which discretion should be used in granting motions to remand:

We generally grant an agency’s motion to remand so long as “the agency intends to take further action with respect to agency decision on review.” Remand has the benefit of allowing “agencies to cure their own mistakes rather than wasting the courts’ and the parties’ resources reviewing a record that both sides acknowledge to be incorrect or incomplete.” Remand may also be appropriate if the agency’s motion is made in response to “intervening events outside the agency’s control, for example, a new legal decision or passage of new legislation.” Alternatively, “even if there are no intervening events, the agency may request a remand (without confessing error) in order to reconsider its previous position.”

These considerations, the court reasoned, supported granting the Service’s motion to remand.

10. Congress has mandated by statute the existence of the Service’s Office of Appeals, has given Appeals a new name, and has provided both taxpayer access to case files and certain rights for certain taxpayers whose requests for consideration by Appeals are denied.

Section 1001 of the Taxpayer First Act amends section 7803 by adding new subsection (e). Section 7803(e) codifies the requirement of an independent appeals function within the Service by establishing “an office to be known as the ‘Internal Revenue Service Independent Office of Appeals.’” According to section 7803(e)(2)(A), Appeals is to be supervised and directed by the Chief of Appeals, who reports directly to the IRS Commissioner.

The legislation largely codifies the existing functions of the Service’s Office of Appeals, but among other features, the legislation (1) provides that the Chief of Appeals has access to legal assistance and advice from the staff of the Office of the Chief Counsel (and provides that the Chief Counsel must ensure, to the extent practicable, that the staff members providing advice and assistance are not otherwise involved in the taxpayer’s matter), (2) requires that access to Appeals generally must be available to all taxpayers, (3) provides that, if a taxpayer who has received a notice of deficiency requests referral to Appeals and the request is denied, the Service must (except in cases involving a frivolous position within the meaning of section 6702(c)) provide a detailed explanation of the basis for the decision and a description of the process for protesting the denial, and (4) requires that “specified taxpayers” (individuals with adjusted gross income that does not exceed $400,000 and other taxpayers with gross receipts of less than $5 million, both figures for the year to which the dispute relates) who have requested conferences with Appeals have access to the nonprivileged portions of the case file on record not later than ten days before the conference.

These amendments generally are effective on July 1, 2019 (the date of enactment), except the requirement concerning taxpayer access to case files, which applies to Appeals conferences occurring after July 1, 2020 (the date which is one year after the date of enactment).

11. You say “FBAR.” We say “FUBAR.” Although Treasury has failed to update relevant FBAR Regulations, the penalty for willful violations is not capped at $100,000 per account, says the Federal Circuit.

Under 31 U.S.C. section 5321(a)(5)(A), the Secretary of the Treasury “may impose” a penalty for FBAR violations, and pursuant to administrative orders, the authority to impose FBAR penalties has been delegated by the Secretary to the Service. Further, under the current version of 31 U.S.C. section 5321(a)(5)(B)(i), the normal penalty for an FBAR violation is $10,000 per offending account; however, the penalty for a willful FBAR violation “shall be increased to the greater of” $100,000 or 50% of the balance in the offending account at the time of the violation.

These minimum and maximum penalties for willful FBAR violations were changed by the American Jobs Creation Act of 2004 (AJCA). The prior version of 31 U.S.C. section 5321(a)(5) provided that the penalty for willful FBAR violations was the greater of $25,000 or the balance of the unreported account up to $100,000. Regulations issued under the pre-AJCA version of 31 U.S.C. section 5321(a)(5), reflecting the law at the time, capped the penalty for willful FBAR violations to $100,000 per account.

In Norman v. United States, the government assessed a penalty of $803,500 for failure to file an FBAR in 2007 with respect to a Swiss Bank account. The taxpayer argued that the “may impose” language of the relevant statute, 31 U.S.C. section 5321(a)(5), provides the Secretary of the Treasury with discretion to determine the amount of assessable FBAR penalties and that, because the outdated regulations had not been amended to reflect the AJCA’s increase in the minimum and maximum FBAR penalties, the Service’s authority was limited to the amount prescribed by the existing regulations.

The Court of Appeals for the Federal Circuit reasoned that the amended statute, which provides that the amount of penalties for willful FBAR violations shall be increased to the greater of $100,000 or 50% of the account value, is mandatory and removed the Treasury Department’s discretion to provide for a smaller penalty by regulation. According to the court, the statute gives the Treasury Department discretion whether to impose a penalty in particular cases, but not discretion to set a cap on the penalty that is different than the cap set forth in the statute.

12. After the Service summarily rejected a whistleblower’s award claim that British Petroleum improperly deducted $12.9 billion in illegal trade or business expenses in relation to the Deepwater Horizon Spill, the Tax Court held it has jurisdiction to review the Whistleblower Office’s decision to reject and denied the whistleblower’s request for remand to the agency.

In Lacey v. Commissioner, Mr. Lacey filed two documents with the Whistleblower Office (WBO) of the Service. The first was a single page claim alleging that British Petroleum (BP) was aware at the time of the Deepwater Horizon incident that the blown well associated with the failure of that offshore drilling platform was releasing between 65,000 and 110,000 barrels of crude per day into the Gulf of Mexico. At $4,300 per barrel, BP would allegedly face a maximum of $47 billion in federal fines. According to Mr. Lacey’s claim, BP engaged in a cover up by pumping chemicals down the wellhead to dissolve or disburse a majority of the spillage into the water column allowing only a small fraction (approximately 1,000 barrels per day) of the crude to surface and be subject to a much lesser fine. He claimed that BP incurred $12.89 billion in clean-up expenses, all of which amounted to a “cover up” to avoid fines and should be disallowed as a deduction for federal income tax purposes.

The WBO analyst who reviewed this first claim recommended that it be rejected and did not provide the claim to an operating division of the Service. The WBO rejected Mr. Lacey’s claim “because the information provided was speculative and/or did not provide specific or credible information regarding tax underpayments or violations of internal revenue laws.” Mr. Lacey thereafter resubmitted a 21-page claim giving additional detail supporting his theory as to why the expenses should be treated as nondeductible. Specifically, Mr. Lacey relied on section 162(f) and asserted that BP should not be allowed a deduction for any funds spent to evade fines or cover up a crime. The WBO again summarily rejected the claim and again the claim was not referred to an operating division of the Service for further consideration.

a. Majority Opinion. In a reviewed opinion (7–4–4) by Judge Gustafson, with which Judges Gale, Lauber, Ashford, Urda, Copeland and Jones agreed, the Tax Court initially addressed whether it has the authority to review the “rejection” of a claim in the absence of “action” and collection of “proceeds” by the Service. In general, section 7623(b)(1) provides that, if “the Secretary proceeds with any administrative or judicial action . . . based on information brought to the Secretary’s attention by an individual, such individual shall . . . receive as an award [a percentage] of the proceeds collected as a result of the action [emphasis added].” Thus, an award may be granted only if there is both a Service “action” and “proceeds” are collected.

Acknowledging that the court does not have authority to order the Service to take action in a whistleblower case, the court considered whether it has authority to review the Service’s decision to summarily “reject” a claim because, on its face, the claim fails to meet minimum threshold criteria in the regulations. The court held that it does have such authority, reasoning that, if the WBO’s determination to “reject” a claim could not be reviewed by the Tax Court, then if the WBO were to completely fail to perform its congressionally mandated function, such a failure would not be reviewable at all. For example, if the WBO simply rejected all whistleblower claims by returning them in the mail, it would be a clear abuse of the WBO’s discretion. Yet the WBO could still prevail by contending that no “action” as contemplated by section 7623(b) had been commenced and no proceeds had been collected on the basis of the whistleblower’s claim. Under such circumstances, the court concluded, the WBO’s rejection of a whistleblower’s claim would be arbitrary and an abuse of discretion subject to reversal by the Tax Court. Thus, the Tax Court concluded that it may review the WBO’s rejection of a claim for abuse of discretion pursuant to section 7623(b)(4), which provides that the Tax Court has jurisdiction to consider an appeal of “[a]ny determination regarding an award under paragraph (1), (2), or (3)” of section 7623(b).

The court then considered whether the WBO’s rejection of Mr. Lacey’s claim reflected an abuse of discretion. The court noted that Mr. Lacey conceded that the WBO had properly rejected his first submission and focused on Mr. Lacey’s second submission. The court concluded that it could not determine whether the WBO gave any consideration at all to Mr. Lacey’s second submission. The Service presented no memoranda or other evidence of recommendations like those that preceded rejection of the first claim. There simply was no explanation for the WBO’s rejection of Mr. Lacey’s second claim. Under these circumstances, the court found that the Service had failed to show, for summary judgment purposes, that there was no genuine dispute as to whether the WBO actually considered even the face of the claim. The WBO’s purported rejection letter did not state the grounds for the rejection in a manner sufficient to enable the Tax Court to review it. The court concluded that the WBO had issued the rejection letter without actual attention to Mr. Lacey’s submission. Therefore, the court denied the Service’s motion for summary judgment on the issue of whether, in rejecting Mr. Lacey’s claim, the WBO had abused its discretion.

With respect to Mr. Lacey’s motion for remand to the agency, the court, referring to its prior decision in Kasper v. Commissioner, noted that, when it reviews a determination of the WBO for abuse of discretion, the court must “decide whether the agency’s decision was ‘based on an erroneous view of the law or a clearly erroneous assessment of the facts.’” In this case, the court concluded, without a meaningful record of the WBO’s decision to reject Mr. Lacey’s claim, the court could not decide whether the WBO’s decision was based on an erroneous view of the law or assessment of the facts. Accordingly, the court reasoned, it would be premature to remand the case to the WBO to articulate a reviewable decision. The court denied the Service’s motion for summary judgment and held that it would issue an appropriate order to obtain the WBO’s administrative record. In doing so, the court also denied Mr. Lacey’s request to remand.

b. Concurring opinion by Judge Thornton. Judge Thornton concurred separately to clarify that the question of whether the WBO abused its discretion in rejecting the whistleblower’s claim would be resolved once the administrative record was reviewed by the Court. Judges Gale, Marvel, Morrison, Kerrigan, Lauber, Urda and Copeland agreed with Judge Thornton.

c. Concurring opinion by Judge Urda. Judge Urda concurred separately to emphasize that the court is not bound to follow the D.C. Circuit’s affirmance of the Tax Court’s decision in Cohen v. Commissioner. In Cohen, the WBO informed the whistleblower that he was not eligible for an award because proceeds were never collected. The whistleblower in Cohen argued that the Service should have acted on his information. The Court held that the WBO’s decision not to act on the whistleblower’s claim was not reviewable by the Tax Court. Judge Urda distinguished Cohen: “The ‘rejection’ category of determination was not instituted until after the D.C. Circuit issued its decision, and that court thus had no occasion to address the issue here, i.e., the scope of our review of such a determination.” Judges Gale, Gustafson, Lauber, Ashford, Copeland, and Jones (in part) joined this concurrence.

d. Dissenting opinion by Judge Buch. Judge Buch dissented in an opinion with which Judges Foley, Nega, and Pugh agreed. He disagreed with the majority’s conclusion that the court must deny the Service’s motion for summary judgment. Judge Buch argued that, because there was no action by the Service and there were no proceeds, there could be no award. In his view, the Service was therefore entitled to summary judgment:

We are authorized by section 7623(b)(4) to review the determination of the amount of an award. Nothing in the statute authorizes us to review the decision whether to proceed with an action, regardless of whether that decision is made in the Whistleblower Office or in an operating division.

XI. Withholding and Excise Taxes

A. Employment Taxes

1. Caught between a rock and a hard place: the “boss told me to do it” defense doesn’t work to avoid liability for trust fund taxes, even when “the boss” is another federal government agency!

In Myers v. United States, the taxpayer was the CFO and co-president of two companies that failed to pay over to the Service withheld employment taxes. At the time, the two companies were owned by a limited partnership parent company, a Small Business Investment Company, that was held under receivership by the Small Business Administration (SBA). The taxpayer maintained that he should not be held liable under section 6672(a) for the companies’ failure to pay over employment taxes because an agent of the SBA told him to “prioritize other vendors over the trust fund taxes,” which he did. After the taxpayer was assessed trust fund tax penalties by the Service under section 6672(a), the taxpayer paid a portion of the assessment and sued for a refund in the District Court for the Northern District of Georgia. The district court granted summary judgment in favor of the government.

On appeal before the Court of Appeals for the Eleventh Circuit, the taxpayer argued that, although the “boss told me to do it” defense was rejected in a number of decided cases involving private companies, the taxpayer’s situation should be treated differently. Here, the taxpayer contended, the “boss” was another federal government agency. Therefore, according to the taxpayer, he was caught between a rock and a hard place: either ignore the SBA or ignore the Service, both of which are federal government agencies. Nevertheless, the Eleventh Circuit, in a per curiam opinion by Judges Tjoflat, Jordan, and Schlesinger, the last of whom was a district judge sitting by designation, affirmed the lower court’s opinion and held against the taxpayer. The court stated that section 6672(a) applies with “equal force when a government agency receiver tells a taxpayer not to pay trust fund taxes.”

In a concurring opinion, Judge Jordan agreed with the result but stated that the decision should be based on narrower grounds. As justification for his concern over the breadth of the court’s holding, Judge Jordan cited McCarty v. United States, in which a taxpayer avoided responsible person liability under the predecessor of section 6672(a) when the U.S. Navy had taken control of a company. Judge Jordan explained that, in his view, the taxpayer’s real argument was that the Service should be estopped from collecting trust fund taxes under section 6672(a) because the taxpayer was acting at the direction of another federal government agency.

Judge Jordan further explained that an estoppel argument by the taxpayer must be based on a finding that the taxpayer’s decision was objectively reasonable under the facts. He pointed to 28 U.S.C. section 960(a), which provides that “[a]ny officers and agents conducting any business under authority of a United States court shall be subject to all Federal . . . taxes applicable to such business to the same extent as if it were conducted by an individual or corporation.” Given this express statutory directive, he concluded that the taxpayer could not have reasonably relied upon the “do-not-pay instructions” of the SBA receiver. Thus, the Service should not be estopped from collecting trust fund taxes from the taxpayer under section 6672(a).

B. Self-Employment Taxes

1. The Service announces that payroll tax compliance is a top priority.

In March and April of 2019, the Service conducted a national two-week education and enforcement campaign to combat employment tax crimes. During these two weeks, the Service visited nearly 100 businesses showing signs of potential serious noncompliance. The Criminal Investigation (CI) Division indicted 12 individuals, executed four search warrants, and saw six individuals or businesses sentenced for crimes associated with payroll taxes. The Service announcement indicated that payroll taxes withheld by employers account for nearly 72% of all revenue collected by the Service. Because of the importance of payroll taxes to the tax system, Commissioner Chuck Rettig stated that “[t]he IRS is committed to compliance in the payroll tax arena, which helps ensure fairness and faith in our tax system.” According to Don Fort, Chief of the Service’s CI Division, “[e]mployers know the rules—they must deposit and report employment taxes accurately—this is non-negotiable.”

To bolster payroll tax compliance, the Service has several tools, including “educational outreach, data analytics, civil investigations by highly trained revenue officers, as well as harsher measures such as lawsuits, seizures and criminal referrals to IRS CI.” Resources on complying with and managing payroll tax obligations are available on the Service website.

2. An author’s trade or business included both writing and developing her brand, and therefore all income she received under publishing contracts, including any portion paid for her name and likeness, was subject to self-employment tax.

In Slaughter v. Commissioner, Karin Slaughter, an author of crime fiction, worked since the 1990s to establish herself as a “brand author,” one who provides prestige or reliable profits to a publishing house. She worked with an agent to obtain a contract with a New York publishing house and with a media coach and publisher to develop her name and likeness into a successful brand. During the years in question, 2010 and 2011, she spent 12 to 15 weeks writing in Georgia, her state of residence, and she also spent time “meeting with publishers, agents, media contacts, and others to protect and further her status as a brand author.”

During 2010 and 2011, she received two types of payments under contracts she had entered into during the years 1999 through 2011: nonrefundable advance payments and royalties based on the sales generated by her manuscripts. The contracts gave the publishers not only the right to print, publish, distribute, sell, and license the works and manuscripts written by the taxpayer, but also the right to use her name and likeness in advertising, promotion, publicity for the contracted works, and the right to advertise other works in her books. The publishing contracts also required the taxpayer to provide photographs and appear at promotional events, and the publishing contracts contained various forms of noncompete clauses. The publishing contracts did not allocate the taxpayer’s compensation in any way, i.e., they neither specified a portion allocable to acquiring the right to print, publish, and license her works, nor did they specify a portion allocable to acquiring the right to use her name and likeness.

On her 2010 and 2011 federal income tax returns, the taxpayer deducted as business expenses the cost of leasing a vehicle to attend media interviews and promotional events, the cost of hosting her own promotional events, and the rent she paid on an apartment in New York City, which she maintained to facilitate her professional activities. The taxpayer’s federal income tax returns for 2010 and 2011 were prepared by a CPA who concluded that the taxpayer’s earned income was the compensation she received for actual writing. This meant that any income she received under the contracts beyond the compensation for writing was payment for the use of her name and likeness, which was “payment for an intangible asset beyond that of her trade or business as an author” and, therefore, not subject to self-employment tax. On the taxpayer’s 2010 and 2011 returns, the advances and royalties were reported on Schedule E, Supplemental Income and Loss, and the payments relating to her trade or business of writing were reported on Schedule C, Profit or Loss from Business. The CPA who prepared the returns allocated the advance payments and royalties to Schedule C based on the portion of the year that corresponded to the time spent writing, which was 12 to 15 weeks. The 2010 and 2011 returns took the position that only the portion of the advance payments and royalties allocated to Schedule C was subject to self-employment tax. The Service argued that all of the taxpayer’s income was directly or indirectly tied to the selling of her books and was, therefore, subject to self-employment tax.

The Tax Court (Judge Wells) held that the taxpayer’s brand was part of her trade or business. Therefore, her income under the publishing contracts was subject to self-employment tax. The court reasoned that she had devoted significant efforts over many years to develop her brand. These efforts included meeting with publishers, agents, media contacts, and others to protect and further her status as a brand author, attending interviews and promotional events, and using social media, websites, and a newsletter to maintain her brand with her readership. The court concluded that “[s]uch sales-focused work is sufficiently routine that we consider it part of petitioner’s trade or business.”

The court also reasoned that the taxpayer’s treatment of her expenses on the returns supported treating the payments received for her brand as part of her trade or business. She deducted as business expenses the cost of leasing a vehicle to attend media interviews and promotional events, the cost of hosting her own promotional events, and the rent she paid on an apartment in New York City. The court concluded that, if brand-related expenditures are deductible on Schedule C, then the income derived from the brand is also income derived from a trade or business.

The court declined to impose accuracy-related penalties for negligence or disregard of rules or regulations because she reasonably relied in good faith on a professional adviser. The court reasoned that she had satisfied the three factors required to establish a reasonable cause defense: (1) the adviser was a competent professional with sufficient expertise to justify reliance because the adviser was a CPA with many decades of experience; (2) the taxpayer had provided necessary and accurate information to the preparer; and (3) the taxpayer, who had no background in finance, law, or tax, actually relied in good faith on the preparer’s judgment.

3. Partners are self-employed, even if they are employees of a disregarded entity owned by the partnership.

The Treasury Department and the Service have finalized, with only minor changes, proposed and temporary amendments to the check-the-box regulations under section 7701. The amendments clarify that a partner in a partnership is considered self-employed, even if the partner is an employee of a disregarded entity owned by the partnership.

Prior to amendment, the check-the-box regulations provided that (1) a single-member business entity that is not classified as a corporation under Regulation section 301.7701-2(b) is disregarded as an entity separate from its owner; (2) such a disregarded entity nevertheless is treated as a corporation for employment tax purposes, which means that the disregarded entity, rather than its owner, is considered to be the employer of the entity’s employees for employment tax purposes; and (3) the rule that the disregarded entity is treated as a corporation for employment tax purposes does not apply for self-employment tax purposes. The Regulations state that the owner of a disregarded entity treated as a sole proprietorship is subject to tax on self-employment income, and the Regulation provides an example in which the disregarded entity is subject to employment tax with respect to employees of the disregarded entity while the individual owner is subject to self-employment tax on the net earnings from self-employment resulting from the disregarded entity’s activities.

The Service’s longstanding position is that a partner is self-employed; any remuneration the partner receives for services rendered to the partnership are not wages subject to FICA, FUTA, and income tax withholding. Nevertheless, some taxpayers apparently have taken the position that, because the regulations do not include an example illustrating how the rules apply to a disregarded entity owned by a partnership, an individual partner in a partnership that owns a disregarded entity can be treated as an employee of the disregarded entity and, therefore, can participate in certain tax-favored employee benefit plans. The final amendments clarify that a disregarded entity is not treated as a corporation for purposes of employing either its individual owner, who is treated as a sole proprietor, or an individual that is a partner in a partnership that owns the disregarded entity. Instead, the entity is disregarded as an entity separate from its owner for this purpose and is not the employer of any partner of a partnership that owns the disregarded entity. A partner in a partnership that owns the disregarded entity is subject to the normal self-employment tax rules.

The Service’s position that a partner cannot be an employee of a disregarded entity owned by the partnership means that compensation to the partner for services rendered to the disregarded entity cannot be reported on Form W-2 and instead must be reported on a Schedule K-1 issued by the partnership. This position also means that such a partner cannot participate in tax-favored employee benefit plans such as cafeteria plans and flexible spending accounts.

The final Regulations apply on the later of (1) August 1, 2016, or (2) the first day of the latest-starting plan year beginning after May 4, 2016, and on or before May 4, 2017, of an affected plan sponsored by a disregarded entity. An affected plan includes any qualified plan, health plan, or section 125 cafeteria plan if the plan benefits participants whose employment status is affected by these regulations.

The final Regulations do not address the application of Revenue Ruling 69-184 (setting forth the Service’s position that a partner is not an employee of the partnership) to either tiered partnerships or publicly traded partnerships. The Preamble to the final Regulations indicates that the Service will continue to consider these issues.

C. Excise Taxes

1. Congress has repealed the Cadillac tax.

Division N, Title I, section 503 of the Further Consolidated Appropriations Act, 2020, repealed section 4980I, which imposed a 40% excise tax on the amount by which the cost of group health coverage provided by an employer (referred to as “applicable coverage”) exceeded an applicable dollar limit. This excise tax was commonly referred to as the Cadillac tax. The repeal is effective for taxable years beginning after December 31, 2019.

2. Congress has repealed the medical device tax.

Division N, Title I, section 501 of the Further Consolidated Appropriations Act, 2020, repealed the 2.3% excise tax on medical devices of section 4191 for sales of medical devices after December 31, 2019.

XII. Tax Legislation

A. Enacted

1. Congress has enacted the Taxpayer First Act.

Section 1001 of the Taxpayer First Act codifies and renames the Service’s Appeals function as the IRS Independent Office of Appeals. Additionally, section 1101 requires that the Service develop a comprehensive customer service strategy, and it requires that the Treasury Department both develop a comprehensive written plan to reorganize the Service and make several significant changes to procedural tax rules.

2. The Further Consolidated Appropriations Act produces a hodgepodge of tax provisions.

The Further Consolidated Appropriations Act, 2020, signed by the President on December 20, 2019, repealed the taxes, commonly known as the medical device tax and the Cadillac tax, that modified the rules for contributions to and distributions from certain retirement plans. Furthermore, the legislation temporarily extended several expired or expiring provisions, and it provided tax relief to those in areas affected by certain natural disasters.

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