Outlook Auto Replies does not work

Larry Magee 0 Reputation points
2026-08-25T18:35:51.6033333+00:00

I've set up an Auto reply message since I'm out of the office today. It seems simple enough, as I watched several how to youtube videos, but it still doesn't work. 

The steps I took were

  1. Settings
  2. Account
  3. Select Automatic Replies
  4. Toggled Automatic Replies to ON
  5. Set Time period from 8am to 5PM today
  6. Created my auto reply message
  7. Selected :Send replies outside your organization
  8. Saved

I refreshed the screen, then sent a couple of test messages from a couple of email addresses and nothing happened

Any suggestions???

Outlook | Web | Outlook on the web for business | Settings
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  1. Hendrix 965 Reputation points Independent Advisor
    2026-08-25T19:05:59.3466667+00:00

    Hi Larry,

    Based on your sharing, your steps are correct and the Auto Replies should work properly. For the best possible assistance, can you share more details about your situation? I greatly appreciate your cooperation and understanding.

    • You said you sent a couple of test messages from a couple of email addresses. Are these internal or external email addresses?
    • Do the test messages reach the Inbox folder of your mailbox or it goes to Spam/Junk email? Exchange does not generate an automatic reply when the incoming message is identified as spam and delivered to Junk.

    Although you have configured Auto Replies feature correctly, there are organization/tenant level configurations that can still block the reply like a mail-flow rule, remote-domain setting, or security service. With your help and more detailed information, we can work together to investigate further and find a solution.

    Should you have any further questions or need additional assistance, please feel free to share them in the comment below. I'm very happy to help.  

    Thank you again for your cooperation and understanding. Hope to hear from you soon.


    If the answer is helpful, please click "Yes" and kindly upvote it.

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