Lawyers · problem and fix
How to compare two Word documents on a Mac: redlining steps for lawyers in 2026
To compare two Word documents on a Mac, open Word and go to Review > Compare > Compare Documents. Pick the original file and the revised file, then click OK. Word leaves both files alone and builds a new copy with every difference marked as a tracked change.
The short answer
- Compare builds a new tracked copy. Your original file stays unchanged.
- The Original box must hold the unedited version you sent out, not the last round.
- Untick Formatting under More >> when you want a text-first redline.
- Track Changes turned on from the start beats any comparison you run later.
- Combine Documents merges several reviewers' copies, two documents per run.
What redlining two versions in word for mac costs you
Hours spent rechecking a bad redline
A comparison against the wrong base file gives a redline that looks clean and hides real edits. You then reread the whole document to be safe. Nobody has measured how long redlining takes lawyers, so no study gives a clean number. The closest figure is the median lawyer pay of $159,670 in May 2025. That works out to about $77 an hour on a 2,080-hour year. That is our arithmetic, not a Bureau of Labor Statistics figure, and it covers all lawyers, not only redliners.
Edits that never reach your screen
The bigger cost is a change you never see. A clause moves, or a number changes, and the compare misses it. The error then carries into the next draft and into the signed version. Track Changes left off from the start is the usual cause. Compare can recover some edits afterward, but it is a fallback, not a replacement for tracked edits.
Hidden data in the file you send
Redlines can carry metadata from earlier drafts, including author names and timestamps. A North Carolina ethics opinion says a lawyer may not search for confidential metadata. If a lawyer sees it by accident, the lawyer must notify the sender. That is one state's rule, not a national one, but it shows the risk. Clean handling of files is a cost you pay in time, not only in risk.
Long review nights on top of heavy work
A 2026 study in the Journal of Affective Disorders found nearly half of working lawyers reported high or very high burnout. The study covers all lawyers and does not measure redlining, so it cannot say comparison work causes burnout. It does show how much pressure already sits on lawyers, which makes avoidable manual checking more costly.
Why it happens
Track Changes was off from the start
If nobody turned on Track Changes before editing, the edits are not tracked. Compare then has to rebuild them from two files. The Journal of Accountancy article calls comparison a narrow fallback for that case, so a clean redline is not guaranteed.
Formatting differences flood the result
Bold, italic, and underline changes and font swaps show up as edits. Each one adds noise. Real legal changes get harder to find, and reviewers start skimming. Formatting is a common reason a redline looks busier than it should.
The base file was already edited
This is the most expensive cause. If the Original is not the version that went out, the redline shows the wrong changes. Edits made in your working copy look like they came from the other side. Teams often do this without noticing, because the file names look alike.
Menu paths differ between guides
Microsoft's Word 2019 for Mac page shows Tools > Track Changes > Compare Documents. Third-party guides show Review > Compare. A reader who follows the wrong guide may not find the command. Check your own menu bar before you follow any written path.
Hidden data travels with the file
Metadata and earlier draft text can sit inside a file you send. A redline does not clear it. People usually notice only when someone else finds it. The cause is a workflow gap, not a single Word setting, so the fix is a habit and a checklist.
How to fix it
These work with or without any app.
Turn on Track Changes before you edit
Open the working copy in Word and go to Review > Track Changes. Turn it on before anyone edits the text. In recent Word for Mac releases, ⌘⇧E also toggles it. If that key does nothing on your version, use the Review tab. Keep it on until the document is final, so every change shows up without a compare step.
Untick Formatting in the Compare window
Open Compare Documents, click More >>, and untick Formatting. Word then ignores changes to bold, italics, and underlines. Use this for a text-first review. Keep Formatting on when font or style changes matter, such as a required filing format. Run that check as a second pass, not as the first one.
Set Original and Revised in the right boxes
Original is the unedited version you sent out. Revised is the version that came back. Before you click OK, read both file names in the dialog. A swap makes insertions look like deletions, and the redline reads backwards. Name your files with dates so the right one is easy to spot.
Use Combine Documents for several reviewers
Go to Review > Compare > Combine Documents. Set Original to the unedited sent copy and Revised to the first reviewer's copy. Turn on Label unmarked changes with and type the reviewer's name. Save the merged file, make it the Original, and combine the next copy as Revised. Combine takes two documents at a time, so repeat this for each reviewer.
Check which version is the base
Before you compare, ask what the other side started from. If a colleague edited your copy after it went out, do not use that copy as Original. Compare against the file that left your office. Write the base file's name in your matter notes so the next person uses the same one.
Read the redline by section
Do not trust a quick scroll. Go section by section and check headings, numbering, defined terms, and tables. Look for whole blocks marked as changed, since a moved paragraph can show up as a delete and an insert. Read your cover email against the redline before you send anything.
Follow your firm's metadata rules
Do not search a file for metadata you were not sent to review. If you see hidden data by accident, stop and follow your state's rule. The North Carolina opinion says to notify the sender and not use the information without consent. Ask your ethics counsel or supervisor when the rule is unclear.
Check Mac support before you buy a tool
Litera's product page names only Windows for its desktop product. Draftable's legal page lists Word but does not state macOS support. Before you buy, ask each vendor for Mac support, the Word versions they support, and current pricing. Do not assume a Windows feature works the same way on your Mac.
Compare two Word documents on a Mac, step by step
Start with both files saved on your Mac. Keep the sent copy and the returned copy as separate files. Open Word, then go to Review > Compare > Compare Documents. A dialog opens with two boxes, Original and Revised. Each box takes a file you pick from a list or browse for.
- Save the sent copy and the returned copy as separate files on your Mac.
- Open Word and choose Review > Compare > Compare Documents.
- In the Original box, pick the unedited version you sent out.
- In the Revised box, pick the version that came back.
- Click More >> and untick Formatting if you want to see text changes only.
- Click OK. Word opens a new document with the differences marked.
Why the Original box matters most
Compare reads two files and reports what changed from the first to the second. Swap the boxes and the report flips. Insertions look like deletions, and a deleted clause looks like new text. Your reader then sees the opposite of what happened. Put the unedited sent-out file in Original every time.
A worked example with a returned contract
Say you sent a services agreement out on a Monday. It comes back on a Thursday with tracked edits. Meanwhile, someone on your team saved a working copy on Tuesday and changed a payment clause. If you compare the Thursday file against that Tuesday copy, the redline hides the Tuesday change. Compare against the Monday file you actually sent. The Tuesday change then shows up as a real change, and you can decide what to do with it.
Compare options in the More window
Under More >> you find extra checkboxes. The table below uses the option names from CustomGuide's Windows walkthrough. Mac menus may use slightly different labels, so match them by name and by meaning.
| Option | What it does | When to change it |
|---|---|---|
| Formatting | Marks bold, italic, and underline changes | Untick for a text-only review |
| Headers and footers | Compares header and footer text | Keep on for signed letters |
| Comments | Compares comments in each file | Untick if old comments are noise |
| Text case | Flags capitalization changes | Keep on when defined terms matter |
| Comparison level | Compares by character or by word | Use word level for clean legal text |
| Show changes in | Puts results in the original, revised, or a new document | Pick a new document for a fresh copy |
Why your redline looks noisy
Most noisy redlines come from formatting. Font swaps, spacing fixes, and style changes show up as edits. Real legal changes then get buried in the noise. Untick Formatting to see the text changes first. Run a second compare with formatting on only when formatting matters for the job.
Track Changes matters too. If it was off while people edited, Compare has to rebuild the edits after the fact. The Journal of Accountancy article calls comparison a narrow fallback for that case. Treat it as a rescue, not a habit.
Nearly half
of working lawyers in a 2026 study reported high or very high burnout, from more than 39,000 respondents
EurekAlert news release on the lawyer mental health study (Krill and Anker)$159,670
Median annual pay for lawyers in May 2025, U.S. Bureau of Labor Statistics
Lawyers: Occupational Outlook HandbookCombine Documents when several people reviewed
Compare handles two files at a time. When three people marked up the same contract, use Review > Compare > Combine Documents instead. Combine also works on two documents per run. Microsoft says the Original should be the unedited version that went out for review. Label unmarked changes so each reviewer's edits carry a name.
- Choose Review > Compare > Combine Documents.
- Set the Original to the unedited version you sent out.
- Set the Revised to the first reviewer's copy.
- Turn on Label unmarked changes with, then type the reviewer's name.
- Keep the first merge set to show changes in a New document.
- Save the merged file, make it the Original, and combine the next reviewer's copy as the Revised document.
Metadata and what it means for your redline
Metadata is information stored inside a file that you do not see on the page. It can include author names, timestamps, and edits from earlier drafts. A redline does not remove it. Before you send a compared file outside your firm, follow your firm's review steps. Your employer's rules on client data come first, every time.
Dedicated compare tools: check Mac support first
Some teams buy a dedicated comparison tool. Litera's Compare product page names only Windows for its desktop product. It says nothing about macOS, system requirements, or price. Draftable's legal page says you can compare from Microsoft Office and Outlook, and it lists Word. It does not state macOS support. Ask each vendor for Mac support in writing, and check their pricing pages before you buy.
Mistakes that waste the most time
- Comparing against a copy that someone already edited.
- Leaving Track Changes off while you edit your own draft.
- Swapping Original and Revised, then reading the output as the truth.
- Keeping Formatting on for a text-only review.
- Assuming a Mac menu matches a guide written for Windows.
- Sending a compared file without checking your firm's data rules.
What to do when the redline still looks wrong
Start with the two file names in the dialog. Confirm which one is Original. Then check the More >> options. If the redline still looks off, open the sent copy from your sent folder and compare again. Read the result section by section. Headings, numbering, and tables often change together, so one missed heading can hide a block of edits.
Where Lazur helps with this job
Lazur is a voice assistant that lives in the notch on your Mac. Hold ⌥ ⌘ to ask about anything on screen, and Lazur answers out loud. Ask where Compare sits and Lazur draws a circle and a label around it. Ask for steps and Lazur guides you one click at a time, waiting for each click. Lazur does not click for you, and it is not a plugin for Word.
Lazur listens and looks only while you hold the shortcut. Audio and the screenshot go to AI providers to answer, and they are not stored. Content is never used to train AI models. If the file holds client data, check your firm's rules before you hold the shortcut over it.
Hold fn to dictate clean, formatted text at the cursor in any app. That helps when you write the cover note that goes with a redline. For the Word side of the job, see the AI assistant for Word on Mac and Microsoft Word for lawyers on Mac. Lazur has a 3-day Pro trial with no credit card, and it starts when you first open the app. Pro costs $18 a month, or $15 a month billed annually. Check the pricing page for current plan details.
Faster with Lazur
Where Lazur helps with redlining two versions in word for mac
Hold ⌥ ⌘ and say what you want. Lazur sees your Word window. Lazur guides you one click at a time and waits for each click.
- 1
Hold ⌥⌘ and talk
- 2
Lazur guides you one click at a time and waits for each click.
- 3
You stay in Word. Nothing to copy into a chat window.
More things to say in Word
- “Where is Compare on my Word menu?”
- “Walk me through comparing these two files”
- “What does Formatting do in this window?”
- “Hold fn and dictate the cover note”
- “Draft a short cover email about the changes”
Free for 3 days, then $18/month. Download for Mac
You say“Walk me through comparing these two contracts”
Lazur · walks you through itYou finish the comparison with the unedited sent copy as Original, one click at a time.
What lawyers say to Lazur for this
Each one is a single hold of ⌥ ⌘.
“Where is Compare on my Word menu?”
Lazur draws a circle and a label around Review > Compare on your screen, so you find it without guessing menu names.
Points at it
“Walk me through comparing these two files”
Lazur guides you one click at a time and waits for each click before it moves on. You still make every click yourself.
Walks you through it
“What does Formatting do in this window?”
Lazur explains the option out loud, so you can decide whether to untick it for this review.
Explains what's on screen
“Hold fn and dictate the cover note”
Dictation types clean, formatted text at your cursor in any app, so the cover note takes less typing.
Types what you say
“Draft a short cover email about the changes”
Lazur drafts the text and types it for you. Read every line before you send it, since the content is yours.
Drafts it
A plan you can start this week
- Day 1
Save the sent version
Save the file you sent as a read-only copy in its own folder. Name it with the send date. Do not edit it after it leaves your desk. This file becomes your Original for every comparison.
- Day 2
Turn on Track Changes
Open the working copy and turn on Track Changes before you touch the text. Check the Review tab to confirm it is on. Keep it on until the document is final.
- On return
Compare the returned file
When the returned copy arrives, open Review > Compare > Compare Documents. Set Original to the sent copy and Revised to the returned copy. Untick Formatting under More >> for a text-first pass.
- Review pass
Read the result by section
Scroll section by section. Check headings, numbering, defined terms, and tables. Ask Lazur to explain any change you do not understand, while the document stays open on screen.
- Several reviewers
Combine the copies
If more people reviewed, use Review > Compare > Combine Documents. Label each reviewer's unmarked changes with a name. Make each merged file the next Original.
- Before sending
Check data rules first
Confirm your firm's rules on client data and metadata before the compared file leaves the firm. If the rules are unclear, ask your supervisor or ethics counsel before you send.
Questions people ask
Can I compare two Word documents on a Mac without buying anything extra?
Compare is built into Word for Mac, so you do not need an add-on. You still need a working copy of Word for Mac. This guide did not check Microsoft's licensing terms, so confirm your plan includes Word before you rely on the steps.
Why does Compare mark almost my whole document as changed?
Usually the boxes are swapped, the Original is not the version that went out, or formatting differs across the files. Check the file names, untick Formatting under More >>, and compare again. A large rewrite in the returned copy can also cause this.
What is the difference between Compare and Combine?
Compare takes two files and produces one revised copy with the differences marked. Combine merges the revisions from two documents and can label each reviewer's unmarked changes. Use Combine when several people reviewed the same draft.
Does Compare change my original file?
No. Microsoft's support page says Word creates a new copy based on the Original. The Original stays unchanged, so keep the sent version safe in its own folder.
Does Word for the web have the same Compare command?
This guide did not confirm it from a Microsoft page. Use Word for Mac for the steps here, and check your own version before you plan a review around it.
Can Lazur run the comparison for me?
No. Lazur points at the controls, explains what you see, and guides you one click at a time. It does not click buttons or edit files for you, so you run the comparison yourself.
What should I do if a returned file has hidden data in it?
Follow your firm's rules and your state's ethics rules. The North Carolina opinion says not to search for confidential metadata, and to notify the sender if you see it by accident. Ask your ethics counsel or supervisor when the rule is unclear.
Sources
- Compare and merge two versions of a document · Microsoft Support · checked 2026-11-07
- Combine document revisions · Microsoft Support · checked 2026-11-07
- Lawyers: Occupational Outlook Handbook · U.S. Bureau of Labor Statistics · checked 2026-11-07
- EurekAlert news release on the lawyer mental health study (Krill and Anker) · EurekAlert · checked 2026-11-07
- 2009 Formal Ethics Opinion 1 · North Carolina State Bar · checked 2026-11-07
- How to compare documents · Journal of Accountancy · checked 2026-11-07
- How to Compare Two Word Documents · CustomGuide · checked 2026-11-07
- Litera Compare · Litera · checked 2026-11-07
- Draftable Legal · Draftable · checked 2026-11-07
Fix redlining two versions in word for mac with Lazur, free for 3 days
Hold a key and ask. Lazur sees your screen, points at the button and talks you through it, in any Mac app. No credit card.