Legal Writing Tools for Mac Lawyers

Mac computers are now the preferred choice for young professionals, including young lawyers and law students. And many other firms have become Mac enthusiasts. Whether you love the interface, the physical design, or whether you got fed up with the Blue Screen of Death and slow forced updates, it’s great to know that more legal tech developers are bringing their products to the Mac platform.

Enterprise Adoption is Growing

According to the 2017 Annual Jamf Trends Survey, Mac and iOS device adoption is increasing at the enterprise level and overall. Nearly half of organizations surveyed (44%) offer employees a choice between Mac and PC, with 73% of employees wanting a Mac if given a choice. And in the 2015 Legal Tech Survey conducted by the ABA’s Legal Technology Resource Center, 8.1% of respondents reported that they use a Mac in their law practice. This number is growing and is slightly higher than Mac’s overall market share (7.3%). That growth is significant and real.

Legal Writing on Macs

Legal writing is an area where Mac-based lawyers have been clamoring for new tech tools for years. Since lawyers spend so much of their time writing in MS Word, there’s been frustration that some of the most lauded tools for writers were not available for Mac users. In the past year, that has changed:

Evaluating Your Options

Still, many lawyers think they don’t need any software other than MS Word for legal writing. In fact, I believed that myself until I tried it. Though MS Word has improved over the years and I’m pretty good at wildcards and find-and-replace, there’s still so much more that I could be doing to raise the quality of my documents—and do it faster. Everyone can benefit from cutting the amount of time spent proofreading and editing. So which add-in, or combination of add-ins, is right for your needs?

Your purchasing decisions will be driven by the challenges you face and the work you do. The four most common challenges are:

  • Checking consistency of spelling, capitalization, formatting, and punctuation
  • Enforcing writing style preferences, including plain language and reducing legalese
  • Properly applying Bluebook rules in litigation documents
  • Substantive definition and cross-reference checking in contracts

No single add-in covers every aspect of legal proofreading and editing. So you should consider where you need the most assistance, what programs you have in place, and how much you’re willing to spend. Since all of the options run within MS Word, they work well together if you choose to use more than one.


Drafting and editing is the most difficult part of any legal writing assignment. It doesn’t matter whether you’re drafting a brief or a contract, it is a feat to craft something that is concise, uncomplex, and not jargon-filled.

WordRake is an editing tool that helps make legal documents shorter and more readable. It improves legal writing style by simplifying and clarifying text, cutting legalese, and recommending plain English replacements. WordRake identifies commonly used legal words and phrases, such as “in addition to,” “pursuant to,” and “in accordance with”—and replaces them with simpler words such as “besides” and “under.” WordRake also fixes passive phrasing and removes redundancies. The user experience is delightful, with no learning required, and all recommendations are shown at once using the track changes feature. Then you need to review each change in context and accept or reject them one by one.

WordRake was first released for PCs in 2012. The Mac-compatible version has been available as a native application for users with Office 2016 since April 2018.


Proofreading, polishing, checking for consistency, and following the leading legal writing style and citation guides is a required part of finalizing any kind of document. It’s time-consuming but necessary. Unfortunately, this part is usually left to the last minute and done poorly. Automated tools are more accurate than any human review.

PerfectIt is a proofreading tool that checks for legal-specific typos, enforces consistency, and conforms your writing to the guidance found in The Red Book: A Manual On Legal Style by Bryan Garner and Black’s Law Dictionary. It will also find formatting, spacing, spelling, and capitalization errors in Bluebook citations.

PerfectIt excels at the tedious task of consistency-checking. Reviewing for consistency requires checking for capitalization of words, phrases, and headings; punctuation of bullet points and lists; hyphenation of prefixes, suffixes, terms of art, and defined terms; paired punctuation, such as quotation marks; and presentation of numbers. It groups consistency errors together and guides the reviewer through each one, using familiar spell-check-like functionality and informative commentary. The reviewer can fix each error with a single click.

PerfectIt was first released for PCs in 2009. The Mac-compatible version became available through the Office Store on June 26, 2018.

Contract Companion

If you are a transactional lawyer, then the accurate substantive use of defined terms and cross-references will be among your main priorities for editing tools. Contract Companion is a drafting and proofreading assistant that helps.

Substantive defined terms checking is the process of checking each definition for proper use. It’s time-consuming because it requires reviewing the definition and use together even though they appear in different locations. Contract Companion will check for defined terms that are used but not defined; defined but not used; and defined more than once or inconsistently. It also sorts defined terms and helps you review based on risk.

For cross-references, Contract Companion will help you confirm that each cross-reference accurately refers to the correct clause or section indicated; and references a section, chapter, or term that actually exists in the document. It provides checking by allowing you to click on the reference, which takes you to the original location. It also offers the option to assign the cross-references (which simplifies Microsoft’s built-in feature).

Contract Companion excels at ensuring consistent substantive use of defined terms and legally-operative phrases. Its two outstanding features are consistent phrase checking that recognizes when you have used similar words but used “of” rather than “and” or have left a comma out, etc.; and risk assessment review and prioritization.

Contract Companion was released for PCs in 2012. The Mac-compatible version was released through the Office Store in April 2017.


It’s an exciting time for lawyers with Macs. Some of the most-discussed proofreading and editing tools are now available. So think about what aspects of proofreading and editing have the biggest impact on your time, take advantage of the free trials offered by all these programs, and find the product that will help you get that time back today.

Check Also

3D printing

How 3D Printing Could Help Prove Medical Malpractice Cases

When products and replicas are produced the traditional way, they require the use of expensive molds and equipment.