How to turn on automatic replies in Outlook on Mac: steps for Microsoft 365

Automatic replies are the messages Outlook sends when you are away from your inbox. Many people call them out-of-office replies. On a Mac, you set them from the Tools menu in the menu bar, and you can set a start and end time so you do not have to remember to switch them on or off. This page gives you the steps for the current Outlook for Mac first, then covers the legacy app, Outlook on the web, and the mistakes that cause the most trouble.

Check your account type before you start

Outlook for Mac only supports automatic replies on some account types. Microsoft says the feature is not supported for Gmail, Yahoo, or other POP or IMAP accounts. If you use one of those, stop here and read the troubleshooting section. Checking first saves you from working through a setting that cannot run.

• Company or organization accounts on Microsoft 365 or Exchange: the case this guide covers.
• Gmail, Yahoo, and other POP or IMAP accounts: automatic replies are not supported, according to Microsoft.
• Accounts where your Exchange admin limits replies: you may see only the inside message box.
• Legacy Outlook for Mac users: the dialog and steps differ, covered in the legacy section below.

Know which Outlook for Mac version you run

Microsoft covers three app families on its Mac page: Outlook for Microsoft 365 for Mac, Outlook 2024 for Mac, and Outlook 2021 for Mac. The dialog labels differ between these and the older legacy app. Current versions use a Set toggle and a Time Period checkbox. Legacy Outlook for Mac uses a reply box labeled Reply once to senders within my organization, plus an Ok button.

Write an out-of-office message people will actually read

Your message is the part people read. In a February 2026 ZeroBounce study of 1,157 professionals in the US and Europe, 71% said they check work email on vacation. The same study found that 26% have no out-of-office message set at all. Many of your contacts may check mail while you are away, so the reply has to do real work.

The same study found that just 29% say their latest message clearly says they will not check email. Say it plainly. Then add when you are back, who handles urgent work, and when you expect to reply.

A 2024 Preply survey of 1,000 Canadian employees found a different pain point. 22% named not giving clear return-date information as the worst out-of-office offense. That survey measures pet peeves, not how often people make the mistake, so treat it as a hint. A clear return date is still an easy fix.

• The day you return, written as a full date.
• Who to contact for urgent work, with an email address or phone number.
• When you will reply to messages that wait.
• A short thank you to the sender, which keeps the tone friendly.

Set the time period and the outside reply

In the current dialog, turn on the Set toggle, then check Time Period. Enter the start and end times. On Outlook on the web, Microsoft says replies stay on until you turn them off if you skip the time period. Pick the end time as carefully as the start, so replies stop when you are back.

The outside message is a separate reply for people outside your organization. Microsoft says it is available if you use a company or organization account. It also depends on your Exchange admin allowing it. If you do not see the box, ask your IT team, because the admin makes that call.

Turn off automatic replies on your Mac

Turn replies off the day you return. Go to Tools > Automatic Replies and switch off Send Automatic Replies. In legacy Outlook, open the same dialog and clear the checkbox for the account. Out-of-date replies confuse colleagues and clients, so do not leave them running.

Reopen the window once after you switch it off. Confirm the toggle reads off. If you also set replies on Outlook on the web, turn them off there too, because that version has its own settings.

Legacy Outlook for Mac: the support dates have passed

Microsoft says support for legacy Outlook for Mac will end in October 2026, and continued support depends on your Microsoft 365, Office, or Outlook license. SMU IT gives a narrower date. It says legacy Outlook for Mac will stop working on October 1, 2026, and will stop connecting to Exchange Online. As of November 7, 2026, both dates have passed. This guide could not confirm whether legacy Outlook still connects today.

SMU IT also warns about the move itself. Local folder backups can take a long time to transfer, so let the transfer finish. Signatures, saved searches, and table editing changed location after the move. Check your signature and saved searches once the move is done.

Use Outlook on the web when the Mac menu is missing

If your Mac app does not show the option, Outlook on the web has the same feature. Select the gear icon for Settings, then choose Accounts > Automatic replies. Turn on Turn on automatic replies, add an optional time period, type the message, and select Save.

Classic Outlook on the web uses Settings > Account > Automatic replies. Choose Send automatic replies, check Send replies only during this time period, and select OK. To turn it off, go to Settings > Automatic replies and select Don't send automatic replies.

Why some guides show a View menu path

You may find a guide that says View > View settings > Accounts > Automatic Replies. Microsoft documents that path on its how-to page. The applies-to list there covers New Outlook for Windows, Outlook 2016 through 2024, Outlook for Microsoft 365, Outlook.com, and Outlook on the web. Mac is not on that list. A third-party guide says the new Mac app uses the View path, but this page could not verify it.

Use Tools > Automatic Replies first. If that item is missing and your account type checks out, test the View path, or use Outlook on the web. Do not guess at other menus.

Common mistakes with automatic replies on Mac

• Writing the message but forgetting to switch on Send Automatic Replies.
• Skipping the Set toggle and Time Period, so the reply has no start or end time.
• Expecting a reply to every email. Outlook sends one reply to each person who writes during your absence.
• Using a Gmail or Yahoo account and wondering why the setting does nothing.
• Forgetting to turn it off, so replies go out after you are back.
• Leaving out a return date, which 22% of survey respondents named as the worst offense.

Test your reply from another account

Send a test from a personal address, not from a colleague's mailbox. An address inside your company only shows the inside message. To check the outside message, send from an address outside your organization, if your admin allows outside replies. Outlook sends one reply per sender, so a second test from the same address may get no reply.

Put a calendar reminder on your return day. That reminder is the easiest way to switch replies off on time, and it takes less effort than remembering it on your first morning back.