A 40-message thread with opposing counsel, three clients copied, and an attachment from last Tuesday. Most lawyers know this inbox. Copilot in Outlook gives you three tools for it: Summarize, Draft, and Coaching. Used well, they save real time. Used carelessly, they can put privileged content in front of the wrong reader.
Here is a workflow that uses all three, plus a 30-second check before you send.
Watch the walkthrough
This 3-minute video uses Summary, Draft, and Coaching by Copilot on a fictitious negotiation email, then finds the privilege problem that Copilot missed.
Read the video transcript
Copilot in Outlook can summarize a thread, draft your reply, and coach your tone. In this walkthrough we use all three on a fictitious negotiation email. Then we run the thirty-second privilege check that Copilot did not run for us.
Here is a fictitious thread in Acme Contractors versus Globex Logistics. Globex’s counsel wants forty-five more days for expert disclosures. Above the thread, a colleague added an internal note. The client will accept thirty days if Globex first produces the text messages. Do not share this with opposing counsel. Select Summary by Copilot at the top of the message. The summary is accurate, and it includes the internal note.
Now start a reply. Outlook offers suggested drafts, and the first one is, agree to 30 days. Copilot built that option from the internal note. It is the client’s bottom line, offered as a one-click reply to opposing counsel. Do not select a suggestion until you know where it came from.
Instead, describe the reply you want. Ours says: decline the forty-five-day request, and offer twenty-one days if Globex produces the February text messages by November 20. Keep it brief and professional.
The draft is short and correct. It does not mention thirty days. Now look below the signature. Outlook includes the full thread in the reply, and the quoted thread includes the internal note: the client will accept thirty days. If we send this as it is, opposing counsel reads our client’s bottom line.
Copilot also says that it did not change the recipient, because it could not verify Laura Pike’s address. In our test, the reply is still addressed to the sender. Always check the To line yourself.
Next, select the Copilot button in the message and choose Get coaching. Copilot reviews tone, reader sentiment, and clarity. Its suggestions are reasonable. It notes that, we can agree, may sound as if the twenty-one days are already authorized, and it offers a more measured version.
Coaching even notices the confidential note. It says that our draft appropriately does not disclose the client’s position. That is true of the words we wrote. It missed the quoted history under them, which discloses that exact position. Coaching checks your draft. It does not check what you are about to send.
So before you send any reply that Copilot helped with, take thirty seconds. Check the recipients. Delete internal or privileged discussion from the quoted history. Check that the draft did not pull facts from an internal email. Confirm the attachments. And make sure the draft does not commit to a date, an amount, or a position you have not approved. Your duty to prevent inadvertent disclosure does not change when an AI tool helps you write.
To learn Copilot in Outlook, Word, and Teams for legal work, take LGTCP101, Copilot for Legal Professionals. For the professional responsibility side, take LGTCP400, Copilot for the Modern U.S. Law Firm. Both are at legalgpts.com.
Step 1: Summarize the thread
Open the conversation. In new Outlook, select Summary by Copilot at the top of the thread. In classic Outlook, select Summarize. Copilot reads the thread and lists the key points. The summary can include numbered references to the messages it used.
If the thread has a Word, PowerPoint, or PDF attachment, new Outlook can also offer Summarize a file.
Tip: Select two or three of the references and confirm that the summary matches the emails. A summary is a reading aid. It does not replace reading the message you are about to answer.
Step 2: Draft the reply
Start a reply. Select the Copilot button on the ribbon and choose Draft with Copilot. Describe what the reply must do. Copilot uses the thread as context, so you do not need to retell it.
Reply to opposing counsel. Confirm we agree to extend the response
deadline by 14 days. Say the extension does not waive any objection.
Keep it under 120 words and professional in tone.Read the draft carefully. Copilot can repeat facts from the thread, including facts that are wrong or that you do not want to share. Edit it as you would edit a draft from a colleague.
Step 3: Coach the tone
For a sensitive message, such as a difficult update to a client, write your own draft first. Then select the Copilot button and choose Coaching by Copilot. Copilot suggests changes to tone, clarity, and sentiment. You choose which ones to apply.
Step 4: The 30-second privilege check
Do this before you send any reply that Copilot helped write.
- Recipients. Is everyone on the To and Cc lines supposed to see this? Look again before you select Reply All.
- Quoted history. Does the message below your reply contain internal or privileged discussion? Delete it if the new reader should not see it.
- Facts in the draft. Did Copilot include anything from an internal email that belongs only to your side?
- Attachments. Are the attachments the correct versions, and are they safe to share with this reader?
- Commitments. Does the draft promise a date, an amount, or a position you have not approved?
Your duty to make reasonable efforts to prevent inadvertent disclosure of client information does not change when an AI tool helps you write. These five checks take less time than a correction letter.
What Copilot can see
Copilot in Outlook works with your mailbox and, with a Microsoft Copilot license, other work data that you already have permission to open. It does not override your firm’s permissions. If those permissions are too broad, Copilot can surface content to people who should not see it. That is a governance issue for the firm to fix before a wide rollout.
Go further
LGTCP101: Copilot for Legal Professionals covers Copilot in Outlook, Word, and Teams, plus prompting and security for legal work. LGTCP400: Copilot for the Modern U.S. Law Firm covers the professional responsibility side, including confidentiality, supervision, and billing.
Sources
- Welcome to Copilot in Outlook, Microsoft Support
- Frequently asked questions about Copilot in Outlook, Microsoft Support
- Draft engaging emails using Copilot in Microsoft Outlook, Microsoft Learn
- ABA Model Rule of Professional Conduct 1.6(c); ABA Formal Opinion 512 (July 29, 2024)
Current as of November 2026. Button names differ between new Outlook, classic Outlook, Outlook on the web, and mobile, and they depend on your license.