September 01, 2015

Secrets to Effective Electronic Documents in the Appellate Process

Sean L. Harrington

This is an article on electronic briefs. But it’s more accurately a commentary on knowing your audience, knowing your rules, and knowing your tools. When I was invited to write on this topic, the editors probably were looking for a straightforward how-to and some encouragement for the continuing adoption of electronic briefs in appellate practices. But there are many excellent publications that do both, including several produced by the American Bar Association. (See the sidebar on page 41.) I thank the editors for extending me the latitude to approach this topic from a somewhat different angle, while remaining faithful to the learning objective: effective utilization of electronic documents for appellate practitioners. (For the purposes of this article, I limit the scope of my discussion to the use of Adobe Acrobat Professional and for briefs that will be opened on computers using the Windows or Mac operating system.)

Since at least 2000, we have been promised that electronic briefs could “change the way judges analyze legal precedent . . . a sort of deeper foundation of the law, or even encouraging judges to search the Web to check factual assertions” (Bradley J. Hillis, “Electronic Briefs in Trial and Appellate Courts,” JURIST, April 20, 2000). As I reflect on some articles styled, for example, “e-briefs and e-filing are e-z” (David L. Masters, GPSolo magazine, June 2004), I feel compelled to share the truth that neither e-briefs nor e-filing has been easy for everyone—including me, a legal IT professional.

Although converting a Microsoft Word document to Adobe Portable Document Format (PDF) is easy enough, and although uploading a document to the federal courts’ Case Management/Electronic Case Files (CM/ECF) system is usually problem free, the disparate policies and technologies used by various courts have proven difficult and confusing for many practitioners. For example, in Minnesota, where I live, the e-filing system requires all documents to be “submitted in searchable PDF format only” (Minnesota General Rules of Practice 14.03), but “No Optical Character Recognition (OCR) data shall be contained in or associated with the document.” Id. at 14.03(b)(2). In reality, what this means is that formatted text—e.g., PDFs converted from WordPerfect, OpenOffice, or Word—are okay, but one must disable OCR when scanning in images (such as a signature page). In practice, I have observed many attorneys struggle to understand how to comply with these requirements.

Aside from the nuances of state court e-filing and federal courts CM/ECF, complex (fully hyperlinked) electronic briefs traditionally have been more difficult and time consuming than mere PDFs converted from word-processing documents and certainly have been more expensive. As I will discuss below, hyperlinked briefs may even be controversial or cost a practitioner the case. But, when utilized effectively, they can be very impactful.

Are Electronic Briefs Permitted, and in What Form?

Perhaps one of the best examples of what can go wrong comes from personal experience: In 2006, I was involved in a case in the U.S. Court for the District of Colorado and endeavored for many days and nights to assemble a substantial filing—a brief in opposition to a magistrate’s recommendation for dismissal—as a complex electronic brief, complete with hyperlinks to trial court filings, cases, and law review articles for the convenience of the judge. Prior to filing, I discussed this plan with the court’s ECF project manager, who confirmed that hyperlinked briefs were accepted and encouraged.

The difficulty with CM/ECF at that time, in contrast to so-called “companion” e-briefs that traditionally were submitted on compact disks to appellate courts, was that it disallowed PDF documents containing embedded-attachment hyperlinks. Consequently, any hyperlink to reference material—anything other than a web resource—had to be appended to the end of the brief. Fortunately, the Electronic Filing Guidelines provided that, “Neither a hyperlink, nor any site to which it refers, shall be considered part of the official record. Hyperlinks are simply convenient mechanisms for accessing material cited in a filed document.” Further, a CM/ECF filing could not exceed 2 MB. Consequently, a fully hyperlinked, self-contained brief—which can easily exceed 30 MB with scanned images (surveys, plats, microfiche records, etc.)—was required to be divided into multiple parts.

The document I filed, had it been printed, was about 68 pages in length. As an electronic document, it was 27 MB in size, so I had to split it into multiple parts. On the first page of each section, I included a conspicuous notice, such as below:

Please note: This is Part B (of 12) of a fully hyperlinked brief pursuant to § H(2)(a) of ver. 2 of the D.Colo. ECF Procedures and which part consists of 6 pages. Pages appearing after page B-6 are for reference only and should not be printed out or construed as if they were incorporated by reference or considered as part of a total page count. (See § X(C) of ver. 2 of the D.Colo. ECF Procedures.)

Between the end of the brief proper and the start of the reference material, I inserted a page with the following notation:


So, what happened? When the trial judge received his notification through CM/ECF that the brief had been filed, he took note of the number of pages stated in the document history display, became very cross, and did not read the brief. Instead, he wrote the following in an order of dismissal:

It is hard to imagine a more frivolous, burdensome, prolix, senseless, and harassing filing than the one containing Plaintiff’s objections. The objections themselves are spread over 2,610 pages, and the exhibits occupy an additional sixty pages. The bulk of the filing consists of an apparently random mixture of copies of cases and exhibits. It is impossible to follow or make sense of this heap, and any attempt to do so would require abandonment of all other cases. . . . The objections to the recommendation are “redundant, immaterial, [and] impertinent,” Fed. R. Civ. P. 12(f) and will be stricken.

To dull the sting of this outcome, I could rationalize that the judge simply didn’t read even the first page of the brief, or that he later resigned his Article III office in response to allegations that he was engaging in conduct in chambers other than reading briefs at about the time frame in question, or that I later obtained some unrelated relief on appeal. But the more sobering conclusion was that the system simply wasn’t conducive for submitting complex electronic briefs, that I was ahead of the times, and that I failed to know my audience.

You can avoid such a mistake by taking the time to understand the limits and capabilities of the e-filing system you are using, and, if you intend to file a “companion” brief on DVD-ROM or other media, by having a frank discussion with court staff about not only whether it will be accepted but also whether it is likely to be used by one or more of the judges on the panel. (Note that, depending on how matters are handled in your jurisdiction, the more invasive the questioning about the judges’ internal procedures or the more prolonged the contact with the judges’ clerks, the more such communications may be vulnerable to allegations of improper ex parte pandering.)

Rules Violations and Impropriety (or the Appearance Thereof)

Know not only your audience, but also your rules. Failure to do so, whether inadvertent or intentional, could result in a brief being stricken, an appeal being dismissed, or the attorney being sanctioned:

  • PDF files can be purposefully laced with so-called web bugs that allow a party to learn when a PDF file was opened and to which page it was read, so long as the reader has an Internet connection. I believe that such surreptitious monitoring could be a violation of ABA Model Rule of Professional Conduct 8.4(c), which prohibits an attorney from engaging in conduct involving deceit, dishonesty, or deception.
  • Every effort must be taken to not include content that the opposing party cannot open. For example, whereas electronic briefs in some jurisdictions may be permitted to include audio, videos, or animations, it may be tempting to include other files, along with the necessary software to open them, to which the opposing party may not have access. This can be perceived as creating an unfair advantage. (See, e.g., Yukiyo, Ltd. v. Watanabe, 111 F.3d 883, 886 (Fed. Cir. 1997), in which the electronic brief gave an unfair advantage because opposing party lacked the technical equipment to view it). Be prepared to provide to the opposing party anything and everything provided to the court.
  • PDF files allow for electronic annotations. One way I have used this is pop-up comments where a rule of evidence or civil procedure or rule of professional conduct is cited: I have made the rule appear as a URL. Instead of being “clickable,” hovering over the text results in a pop-up containing the rule text. As this is no different than including a copy of the rule as part of the appendix, this is not likely to violate word count regulations in many jurisdictions, but if this feature is used to provide commentary (i.e., argument), it surely would add to the word count, and it would not be visible in the paper brief that opposing party may, instead, be reviewing.
  • If you are filing a companion brief, and assuming the appellate judges eschew the paper brief in favor of your electronic brief, they or their clerks may not be checking for the accuracy of the hyperlinked supplemental material. In other words, the electronic brief could provide an opportunity to circumvent the certification of the record on appeal by including additional content that was not properly preserved. This could be a hyperlink to an alias of a trial court pleading but which itself has links to materials outside the record (e.g., photographs), or it could be a hyperlink to falsified motions, deposition transcripts, case law, or even a website created or operated by the attorney or the client made to appear as an authoritative blog or that contains impermissible content outside the record. Although I do not need to explain why such subterfuge would likely result in the most harsh consequences for both the client and the attorney, innocent practitioners experimenting with electronic brief technology must assiduously resist any temptation to include additional material that is not properly preserved. Even linking to an enhanced or clarified—but different—image or plat map than was available in the lower court proceedings could be viewed as an impropriety.

Stability and Convenience

When assembling an electronic brief, you probably will want to configure each link to open in a new window. (This is done by editing the properties of each hyperlink.) The reason is that, if readers click on a link that takes them to a different document, they may not know how to navigate back to the master document (your brief) and must reopen it, thus losing their place—very annoying. However, if every link opens as a new window and your readers are in the habit of minimizing linked documents, the readers’ computer could crash. (This obviously detracts from the desired objective of using technology to facilitate persuasion.) This is because a PDF file with myriad hyperlinks to other PDF files (either embedded within the master PDF or via a relative path to another directory on the media) that open in new windows can result in scores of PDF files open on the reader’s computer. Eventually, these scores of minimized documents consume so much system resources that the computer becomes unresponsive.

The way I have overcome this dilemma is to create an action button at the top right of every page of every linked PDF that is eye-grabbing green and labeled “Back” with an arrow:

This “back” button, which uses a custom icon, is actually a trick: Clicking on it closes the linked PDF, returning the user to the master PDF. (Under button properties, the Select Trigger for this button is “Mouse Up,” and the action executed is “File>Close.”)

Another convenience feature is to include an active table of contents. In Word, for example, if you use the insert TOC feature and then convert to PDF, Acrobat bookmarks will be automatically created. You may also want to edit the properties of the PDF such that the initial view is “Bookmarks Panel and Page.” This way, navigating your brief from section to section is very easy to do. Keep in mind, however, that the bookmarks panel will take up screen real estate, but also that the user can close that panel easily. Also, if you are embedding attachments within the master PDF (and this is not disallowed by the e-filing system you are using), you would not want to have the initial view be “Attachments Panel and Page” because seeing hundreds of attachments in a panel at the bottom of the page would likely be distracting for any reader.

A feature that I mentioned earlier is the hover-over comment feature. I accomplish this by making the desired text appear to be a hyperlink: To do this, I make that text blue (matching the real hyperlinks), then use the “underline text” feature (an Acrobat annotation tool) with a line color that matches the blue, and I make sure the “Author” field for the underline properties is null. Now, when the reader moves the cursor over the blue underline text, a comment immediately pops up but does not show an author name. This is useful for providing rule or statute text (if short). Figure 1 shows a pop-up where the cursor is over § 1331.

Longevity and Validity of URLs

Concerns of URL permanency have been raised for years: One professor lamented, “Too many recent opinions rely upon questionable or non-available sources, and such misplaced reliance certainly cannot be what judicial authors wanted or intended” (Coleen Barger, “On the Internet, Nobody Knows You’re a Judge: Appellate Courts’ Use of Internet Materials,” Journal of Appellate Practice and Process, Fall 2002 (4:2)). Another enumerated many of the benefits of digital briefs and e-filing, yet pointed out that, “Ironically, the benefits of shifting to e-briefs may actually diminish our ability to successfully archive the information we are attempting to preserve” (Michael Whiteman, “Appellate Court Briefs on the Web: Electronic Dynamos or Legal Quagmire?,” Law Library Journal, Summer 2005 (97:3): He worried that future changes to the format in which these files were created may no longer be readable by future technology standards. For this reason, external sources should be selected carefully based on both quality and probable longevity, as it may be several months before the briefs are reviewed.


Complex electronic briefs can be a powerful tool of persuasion, and, if done correctly, can greatly simplify the work of appellate judges and their law clerks. Unfortunately, owing to inconsistencies between the state courts (including differences between a state’s trial and appellate court e-filing systems) and design limitations in the federal CM/ECF system, or else owing to express or unwritten procedures, many practitioners are limited to filing electronic briefs with reduced functionality. To get the most out of your electronic brief usage and dollars, know your audience, know your rules, and know your tools.

Further Resources

Deborah Ausburn, "When to Use Hyperlinked Briefs," TGL Media, 2004:

Brett Burney, "How to Build Electronic Briefs," GPSolo magazine, June 2010 (27:4):

Mark A. Jess, How to Use Virtual Briefs," ABA Employment Law Section Technology Committee Midyear Meeting 2002, May 15-17, 2002:

David L. Masters, "e-briefs and e-filing are e-z," GPSolo magazine, June 2004 (21:4):

Daniel Sockwell, "Writing a Brief for the iPad Judge," Columbia Business Law Review, January 14, 2014:

Michael Whiteman, "Appellate Court Briefs on the Web: Electronic Dynamos or Legal Quagmire?" Law Library Journal, Summer 2005 (97:3):

Sean L. Harrington

Sean L. Harrington ( is a cyber-security practitioner in the banking and health care industries and a digital forensics examiner. He is admitted to the California bar and licensed to practice digital forensics in Texas, and he teaches computer forensics in Century College, Minnesota.