Microsoft has started rolling out a new capability for its Copilot AI assistant in Outlook: it can now draft your automatic replies when you’re away from the office. The feature, which began reaching Microsoft 365 Copilot subscribers in early 2025, means you no longer need to stare at a blank window while crafting the perfect out-of-office message. Instead, tell Copilot why you’re gone—a vacation, a business trip, a sick day—and it will generate a cordial draft that you can approve, edit, or discard.

What Changed in Outlook

Until now, setting up an automatic reply in Outlook involved typing your own message from scratch or reusing a stale template. With this update, users with eligible accounts will see a “Draft with Copilot” button when they open the automatic replies panel. Clicking it opens a text field where you can jot down a few key points: where you’ll be, how long you’ll be out, who to contact in your absence. Copilot then writes a complete message—complete with a subject line, greeting, body, and closing—based on that prompt.

The feature is part of a broader Copilot integration into the new Outlook for Windows and Outlook on the web. Microsoft is rolling it out gradually, so not everyone will see it at once. According to Microsoft’s support documentation, the feature requires a Microsoft 365 Copilot license, a mailbox hosted on Exchange Online, and the UI language set to English. Mobile apps (iOS and Android) do not currently support the drafting feature, though users can see and turn on automatic replies drafted elsewhere.

Copilot doesn’t just paste your raw notes; it formats them into a polite, professional tone. For example, if you type “on PTO next week, back June 5, contact Sarah for urgent stuff,” Copilot might generate: “Thank you for your email. I’m currently out of the office on personal leave, returning on June 5. For immediate assistance, please contact Sarah at [email protected]. I’ll respond to your message when I return.” You can then edit the text before saving the automatic reply.

How It Affects Different Users

For everyday workers

This is a genuine time-saver. Writing an out-of-office message might seem trivial, but many people overthink the wording, worry about tone, or forget to include vital details like return dates. Copilot removes the guesswork. However, it’s wise not to treat the AI as infallible. Double-check the draft for accuracy: does it mention the correct alternative contact? Is the return date right? Does the tone match your workplace culture? A quick review ensures you don’t broadcast errors to everyone who emails you while you’re away.

For IT administrators and managers

The feature raises governance questions. Copilot drafts rely on your mailbox data and your prompt, but the AI processing happens in Microsoft’s cloud. Tenant admins should confirm that this capability aligns with their data residency and compliance requirements. Microsoft says it handles data in accordance with existing Microsoft 365 privacy controls, but admins may want to review Copilot settings and share guidelines with users about what to include in prompts. The feature is visible to users by default, but administrators can check the Microsoft 365 admin center message center for rollout specifics and any available toggles. For organizations that haven’t fully embraced Copilot, it might be time to clarify which tools are approved for drafting external-facing communications.

The Broader Copilot Rollout

This out-of-office drafting feature is the latest step in Microsoft’s aggressive push to embed Copilot across its productivity ecosystem. Copilot first appeared in Microsoft 365 apps in late 2023, with Word getting AI-generated document drafts, PowerPoint adding slide creation, and Excel introducing formula writing. Outlook received an early feature: email summarization for long threads. In 2024, Microsoft added Copilot to the email compose window, letting users draft entire messages from prompts. The new out-of-office integration extends that compose capability to the specialized auto-reply scenario.

Microsoft has been clear that Copilot in Outlook is designed to handle the drudgery of email writing, not to replace human judgment. The automatic reply draft feature was initially spotted by beta testers in the Microsoft 365 Insider program earlier this year and has since trickled out to production. Its arrival aligns with a larger trend of AI assistants managing routine communications, from Google’s “Help me write” in Gmail to third-party tools like Grammarly. For Microsoft, it’s another way to demonstrate Copilot’s value and drive adoption of the premium licensing tier.

What You Should Do Right Now

If you have a Microsoft 365 Copilot license and use English-language Outlook, try the feature the next time you prepare an out-of-office message. Here are four practical tips:

  1. Check your access: Open the new Outlook or Outlook on the web, go to View > View settings > Accounts > Automatic replies (or File > Automatic Replies in classic Outlook if supported). Look for the “Draft with Copilot” button. If you don’t see it, ensure you’re on the latest version and that your admin hasn’t disabled it.
  2. Start with a clear prompt: Instead of a vague note, give Copilot specifics: “I’m on vacation from May 10 to 17, no email access, contact James Lee at [email protected] or call my cell at 555-0199 for emergencies.” The more detail, the better the draft.
  3. Always review and edit: AI drafts can sometimes miss nuance. Read the entire message aloud before saving. Adjust the tone, add personal touches, remove any placeholder details that don’t apply, and confirm that alternative contacts are correct.
  4. Don’t share sensitive information in prompts: Treat any AI tool as potentially observable. Avoid feeding it personal data or internal-only details that shouldn’t be processed in the cloud.

For administrators: Monitor the message center for announcement IDs related to this rollout. Consider communicating best practices to users, and evaluate whether to leave the feature enabled by default or restrict it until you’ve assessed compliance impact. No specialized policy controls are required beyond existing Copilot governance, but it’s worth confirming with your Microsoft contact.

What to Watch For

Microsoft will likely expand the feature in the coming months. Support for multiple languages beyond English is an obvious next step, given that automatic replies are global. Integration with your calendar to auto-populate dates and even suggest alternative contacts based on meeting overlaps could make the process even smoother. A snooping feature that analyzes incoming emails to tailor out-of-office responses dynamically might also be on the roadmap, though that raises privacy questions.

More broadly, the line between Copilot and basic Outlook functionality may blur. If adoption spikes, Microsoft could eventually offer a lightweight auto-draft tool to all Microsoft 365 subscribers, much like how some AI features in Word have trickled down. For now, the feature remains a premium perk, but it’s another signal that AI is becoming an integral part of how we manage email. The days of agonizing over the perfect out-of-office phrasing may finally be over—if you’re willing to let Copilot do the typing.