Mediating a Holy War Windows vs. Mac vs. Linux

By Aaron J. Rittmaster

Since the introduction of Windows for Workgroups 3.11 at the end of 1993, Windows has been the operating system of choice in most law offices. But as we enter the second decade of the Internet Era, operating systems other than Windows are once again viable alternatives in the law office, especially for solos and in small firms. Compelling arguments can be made for both Mac OS X and Linux. The key is to recognize that, like all other law office technology, an operating system is a tool used to complete work. Choosing the right tool is a matter of weighing the costs and benefits of each option.

Windows: Office OS Orthodoxy

Windows has been the default operating system (OS) for law firms for close to two decades. Its ubiquity may be its biggest asset. Windows’ market share means that there’s a large catalog of software titles available, plenty of choices of hardware peripherals, a ready supply of technical support, and a familiar interface for most users. To some extent, however, Windows’ strengths are also its downfall. The availability of abundant software choices is great, but it also leads to inevitable incompatibilities. To compound this problem, Windows installation routines often stash files in obscure locations, so removing software that is causing conflicts can be maddeningly difficult. The Windows registry, the central repository of Windows configuration information, can become bloated and slow as more programs are installed. Hardware support has similar problems. By opening its platform to the largest universe of peripheral suppliers possible, Windows has allowed itself to be polluted by poorly written drivers that lead to system instability.

Although technical support is readily available for Windows users, the quality of that support can be spotty. When there’s a huge user base to support, the ability of support providers to keep up with the demand leads to script-driven support that too often begins with, “First, reformat your hard drive.” User familiarity with Windows means that most new hires can hit the ground running with a Windows computer system, but this familiarity also can lead to user laziness. Powerful features (especially those found in right-click context menus or buried in the Control Panel) go unexplored and undiscovered.

If you do choose Windows as your operating system, the next decision to be made is “old reliable” Windows XP or the “latest and greatest” Microsoft Vista. At this time, my unequivocal recommendation is that Windows XP Pro is the better option. Although XP certainly has its flaws, those flaws are generally well-known, and strategies have been developed already to deal with them. Vista will have been on the market for about 18 months by the time this article is published, and its major drawbacks are apparent. First, Vista requires substantially more powerful hardware to run than does XP. Based solely on the published system requirements (which are always at the very low end of barely adequate), Vista requires three times the processor power, four times the system RAM, at least twice the video card capability, and ten times the hard drive space as XP. And, according to studies posted to and c|net in 2007, even with that more powerful (and more expensive) hardware, XP outpaces Vista in performing common business computing tasks by somewhere between 22 percent and 125 percent, depending on the underlying hardware (see and In addition to the greater expense and slower performance of Vista, hardware and software compatibility continue to be problematic under the new operating system. Finally, Vista’s most-touted security improvement, known as User Account Control (UAC), is so annoyingly implemented that even highly security-conscious users frequently choose to disable UAC rather than put up with it.

Mac OS X: The Progressive Alternative

For as long as law offices have been running on computers, it seems, the oddballs and iconoclasts who refuse to use Windows have turned instead to Apple Macintosh computers. Mac users have always been in the minority, but Mac supporters are a passionate, devoted lot. With Apple’s shift from Motorola to Intel processors and the resulting ability to run either Windows- or Mac-native software, Macs have been quietly gaining ground on Windows-only systems.

Unlike Windows, OS X runs only on Apple hardware. This unified software/
hardware approach contributes to greater stability and a more positive user experience than is generally found in the Windows world. Security is also stronger because of OS X’s UNIX-derivative core. Thus far, only one virus that can infect a Mac computer has actually been identified in the wild.

For the law office, software choice for the Mac can be a concern. True, law office-specific software for the Mac is scarce as compared to that available for Windows. However, platform-independent options and software offered directly by online application service providers (ASPs, also known as “software as a service,” or SaaS) are becoming ever more prevalent in this Web 2.0 world. From a functional perspective, there are few—if any—software applications that are completely unavailable in the Mac world. Although a specific title may not be available, another application that performs the same function is. For that rare occasion when there is a “must have” Windows-only application, there are now many different ways to run Windows and Windows applications on an Intel-based Macintosh computer—either in a virtual machine using Parallels or VMWare Fusion, under software emulation in CrossOver Mac, or natively via Boot Camp.

Any Mac currently shipping is running the latest version of OS X, version 10.5, known as Leopard. Although there have been some reports of problems when users upgrade to Leopard from earlier versions of OS X, new machines running Leopard have generally been problem-free. The move to Leopard initially caused incompatibilities with some software, in particular software that used a feature called “input managers,” which were substantially changed in Leopard, but most such software has already been updated to become Leopard compatible. Leopard did add one particularly compelling feature—Time Machine. Time Machine can maintain a continually updated backup of your entire system on an external hard drive. Did you accidentally delete a critical file back on April 1, 2008? Select “April 1, 2008” in Time Machine, and your entire system will roll back to its exact state as of April 1, 2008. Choose the file you need to retrieve and click “Restore,” and Time Machine brings your system back to the present (with the addition of your missing file). Time Machine can even be used to do a complete system restore. How far back in time you can go is limited only by the size of your backup drive.

Lawyers currently using Macs in their law offices extol its “bang for the buck” power, ease of use, and stability. Macs may look more expensive than their Windows counterparts at first glance, but if the comparison is between machines with equivalent components, the pricing is very similar. The only real difference is at the very low end of the Windows spectrum. Apple has chosen not to compete at the bottom end of the scale on features and components. My own experience with bottom–tier Windows machines is that buyers’ remorse is almost inevitable. For example, a bottom-tier Windows box I purchased from a major vendor only three years ago had a motherboard that supported a maximum of 1 GB of RAM and had space for only one internal hard drive. I recently had to retire that box out of frustration when trying to troubleshoot a failure.

The Mac operating system is generally less resource hungry than is Windows, so users report much greater performance benefits for the same monetary investment (although maximizing installed RAM is still one of the most reliable ways to maximize performance). Most attorneys using Macs also claim to be saving money on technical support, at least in part because the more intuitive OS X user interface makes it easier to troubleshoot quickly for oneself. The stability issue is probably best exemplified by Mac laptops. As the owner of a MacBook, I almost never shut down my computer. If I’m not using the laptop, I just close the lid and it goes to sleep. When I open the lid back up, the system pops right back up. I tried that with my previous laptop—running Windows XP Pro—but it usually led to a hard reboot after failing to resume from the hibernation state.

Macs also have been beating Windows machines with regard to “total cost of ownership” (TCO) for close to a decade now. Because, as mentioned above, the hardware costs are essentially even for Macs and Windows machines, the real differences come when analyzing user output. Consulting firms such as GISTICS and Gartner have reported that Mac’s ease-of-use leads to fewer help desk calls, and therefore lower tech support costs. Also cited as Mac benefits in the TCO category are less downtime per user, fewer reboots, simpler system maintenance and administration, and less expensive upgrades. Relative to Windows machines, Macs tend to have a longer usable life, with office users getting as much as six years of life out of a Mac, rather than the three years most get from a Windows computer.

The single greatest complaint from lawyers contemplating a switch to the Mac OS X platform is the lack of Mac-native practice management software and the lack of some practice area-specific niche software tools. There are practice management tools on the market for the Mac. LawStream ( and Daylite ( appear to be the two favorites among Mac-using lawyers right now. But it is true that there are fewer choices on the Mac side than there are in the Windows world, and many lawyers complain that the Mac applications that are available just do not seem to “fit” with their practices. For true sole practitioners, another recently introduced option is Bento, from the makers of FileMaker Pro ( Bento is touted as an easy-to-use personal database. It lacks the networking, e-mail integration, and mobile device synchronization features of higher-end products, but users of the Bento beta software have been effusive in their praise of its incredibly easy drag-and-drop interface for creating a custom database. Other options exist in the world of ASP/SaaS products that run in a web browser and are operating system neutral, or even LAN-based programs that run in a browser, such as the DeskNow ( groupware software that I wrote about in the June 2006 issue of GPSolo (“How to Be Mobile on the Cheap,”

The options for dealing with niche software products, such as child support calculators and jurisdiction-specific probate software, may be more limited. Often, such products are developed exclusively for the Windows platform. However, this problem can usually be overcome with the assistance of the Windows virtualization and/or emulation software solutions referenced above.

Linux: New Age Computing (for Free)

For the technically inclined, Linux is increasingly a viable alternative. Linux has been gaining market share in the back office for years and is a favorite for small-
office servers. But Linux is becoming a usable option on the desktop as well. Distributions such as Ubuntu and PCLinuxOS provide a first-boot experience that is very close to the first-boot of a Windows machine. Although its desktop resembles that of Windows, the Linux file system is substantially different from the Windows file system—mostly in good ways (more file system options, greater security), but different nonetheless. Drives of all types (internal and external hard disks, flash devices, optical drives, etc.) are represented as files rather than as drive letters.

Linux offers two particularly compelling advantages over either Windows or Mac OS X: cost and efficient hardware use. Although you can choose to pay for a Linux installation—which usually comes with a support contract—most Linux distributions (known as distros) are available to download for free. Donations are usually accepted, but no payment is required (or even really expected). Most necessary software is also available for free. Indeed, the heart of Linux is the concept of Open Source software, which is free to use and free to distribute, with source code open to public examination, criticism, and modification. Linux is much more hardware efficient than either Windows or Mac OS X. As a result, older Windows hardware often can be repurposed to run Linux with a notable increase in computing speed and responsiveness.

But Linux is not without its drawbacks. There is no polished law practice management software currently available for Linux. Platform-neutral ASP/SaaS solutions are just about the only option at this time (unless you’re prepared to write your own
applications). But plenty of good options exist for general business software. is an excellent alternative to Word/Excel and interoperates well with both Word and WordPerfect. Web browsing on Linux using Firefox is almost identical to browsing using Firefox on Windows or Mac computers. A plethora of free e-mail clients are available on Linux, from the Outlook-like Evolution to the Firefox/Mozilla-based Thunderbird. As such, Linux can be a great option for support staff computers. All the software needed for support staff to compete their tasks is readily available, without the Windows risks of viruses and malware. There are emulation options on the Linux side as well, which allow Linux computers to run some Windows software.

On the Open Source front, there is the Wine project, which can be remarkably successful running Windows software but also can be difficult to configure. Wine stands for “Wine Is Not an Emulator”; rather than emulate Windows, Wine allows Windows programs to run under a Linux operating system through the implementation of a software compatibility layer. CrossOver Linux, like CrossOver Mac, is a commercial product built on the Wine framework and offers easier configuration though somewhat less flexible functionality.

Linux also has drawbacks on the hardware side. Linux support for peripherals can be spotty, and getting peripherals to work right can be challenging. Unfortunately, even where peripheral drivers are available, they sometimes offer only limited functionality. For example, the HP 3380 multifunction device in my wife’s office prints under Linux, but the scanning and fax-from-desktop capabilities of the device are unavailable. Careful research, usually involving searches of online user support forums, is often necessary before making Linux peripheral choices.

Ultimately, Linux can be an excellent option for those willing to invest the time and effort into learning to use it. Linux’s advantages are in its low cost (thanks to reduced hardware requirements), free software licensing, and excellent record of preventing downtime in use. The learning curve can be steep, but once users are brought up to speed, Linux has probably the lowest TCO of all current options (if your firm can live with the lack of available law practice-specific software titles).

An Ecumenical Solution

Computer operating systems are tools. The key is to make the best use of tools to maximize law office productivity while minimizing the costs of buying and maintaining equipment and supporting users. Because Windows, Mac, and Linux computers all communicate well with each other in this age of the network, it’s not even necessary to choose only one option. My wife’s law office operates quite smoothly right now with a combination of an Ubuntu Linux server, a Windows XP Pro desktop, and a Mac OS X laptop used for remote work. We’ll likely replace the XP Pro machine with an OS X machine when it is next due for an upgrade, but that’s more a matter of convenience than anything else (because I’m not giving up my MacBook). Rather than being caught up in product evangelism for one platform or another as a matter of pseudo-religious doctrine, lawyers serve themselves, their law offices, and their clients best when computing choices are made based on productivity, reliability, and efficiency. 

Aaron J. Rittmaster is an attorney and technology geek in Overland Park, Kansas. He may be reached at .

Copyright 2008

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