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How to Set Up Automatic Reply in Outlook (All Versions)

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Outlook is the email client made by Microsoft used by millions of people for work email, calendar and contact management. But sometimes you want to set up an automatic reply for many reasons, e.g., you are going on vacation, you are out sick, you switched jobs and want to redirect emails or you just need a break from inbox notifications.

Quick fix. Outlook calls this Automatic Replies or Out of Office. Different versions hide the setting in different places. Real talk, the new Outlook for Windows changed the menu in 2024 and a lot of people cannot find it.

This easy guide will help you set up an automatic reply in Outlook by walking you through the desktop, web and mobile steps, explaining how to set different messages for internal and external senders and helping you fix the issue where auto replies stop sending.

Method 1: Automatic Reply in Outlook Web

This is the easiest path. Works whether you use Outlook on Mac, Windows or any browser.

  1. Go to outlook.com or outlook.office.com.
  2. Click the gear icon at the top right.
  3. Click Automatic replies.
  4. Toggle Turn on automatic replies.
  5. Set a start and end date if you want it scheduled. Skip to set it on indefinitely.
  6. Type your message in the box.
  7. Optionally check Send replies outside your organization and write a different message.
  8. Click Save.

Done. Outlook sends your reply to every incoming email until your end date or until you turn it off.

Method 2: Automatic Reply in New Outlook for Windows

The new Outlook for Windows app uses the same path as web.

  1. Open the new Outlook app.
  2. Click Settings (gear icon) at the top right.
  3. Click Accounts > Automatic Replies.
  4. Toggle on, set dates and message.
  5. Click Save.

Same outcome as web version. Microsoft is unifying the experience.

Method 3: Classic Outlook Desktop (Older Versions)

If you still use the classic Outlook desktop app:

  1. Click File in the top menu.
  2. Click Automatic Replies (Out of Office).
  3. If you do not see this option, your account is not on Exchange. Use a rule instead (see below).
  4. Select Send automatic replies.
  5. Set date range if needed.
  6. Type your reply in the Inside My Organization tab and Outside My Organization tab.
  7. Click OK.

The Inside tab message goes to coworkers. The Outside tab goes to everyone else. Customize each as you want.

Method 4: Automatic Reply with a Rule (Gmail or Non-Exchange)

If Outlook does not show the Automatic Replies option, you are likely on a personal Gmail or POP account. Use a rule instead.

  1. Create a new email with your auto-reply message.
  2. Save it as a template (File > Save As > Outlook Template).
  3. Go to File > Manage Rules & Alerts.
  4. Click New Rule > Apply rule on messages I receive.
  5. Skip conditions to apply to all messages.
  6. Choose Reply using a specific template and pick your template.
  7. Save the rule.

One catch. Outlook has to be running on your computer for the rule-based reply to actually send. Web-based replies work without your PC on.

What to Write in Your Out of Office Reply

Skip the cliche. Real talk, keep it short. Three things:

  • When you are back. Be specific. Monday October 15.
  • Who to contact in the meantime. Coworker name and email for urgent stuff.
  • Whether you will check email. Say no if you actually will not check. People appreciate the honesty.

Skip the full life story. Five sentences max.

What If Auto Replies Are Not Sending

You set it up but people say they did not get a reply. Common reasons:

  • Outlook only sends one auto reply per sender per session. Repeat senders only get it once.
  • If you used a rule, Outlook has to be running.
  • Your IT admin disabled external auto replies for security. Internal still works.
  • The start date has not arrived yet.

Check those before assuming it failed.

My Honest Opinion

Most out of office messages are too long. People are not reading novels. Three lines is plenty.

Personally I always set the end date one day after I actually come back. Gives me a buffer to catch up before being expected to respond.

Final Thoughts

Setting up an automatic reply in Outlook takes a few clicks in Settings on web or desktop. Different message for internal versus external senders is supported.

Also, if you follow our steps and still face difficulties setting up automatic replies in Outlook, seek help from Microsoft Support or leave a comment in the comment section of our blog.

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