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Outlook Not Sending Some Emails But Says They Were Sent and Deletes the Email RRS feed

  • Question

  • My co-worker recently began experiencing an issue with Outlook where she will reply to some emails but the email never arrives at it destination.  Additionally, Outlook says a reply was sent (even displaying the return arrow) but then does not have a copy of the email in the Sent Items box or show the email in the Conversation view when you select "Find Related Messages."

    We are using Microsoft Exchange and running Office 2016 on Windows 10.

    Tuesday, March 19, 2019 11:44 PM

All replies

  • Hi Scott HD,

    Can you reproduce this issue on the web mail?

    Please also check Junk Email and Deleted folder to see if sent messages exist.

    In case the profile was corrupted, please create a new profile to test the result.

    If issue continues, we can try opening Outlook in safe mode to see if the issue continues. Please exit Outlook, press Win key + R to open the Run command, type outlook.exe /safe and then press Enter. This helps eliminate whether the problem lies on any third party add-ins.

    Any updates, please feel free to post back.

    Regards,

    Perry


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    • Proposed as answer by Perry-Pan Thursday, March 21, 2019 3:06 AM
    Wednesday, March 20, 2019 3:15 AM
  • What does the Exchange server message tracking logs show?

    Get-MessageTrackingLog -Sender sender_Address -Start date dd/mm/yyyy 

    Does this show as successful?

    Are you using any mail filtering products or add-ins?  Try disabling these before sending a new message.

    Can you send an email to this user and have them reply successfully? Or is it only when they compose emails?

    Wednesday, March 20, 2019 3:32 AM
  • Hi Scott HD,

    Just check if there are any updates with this issue?

    Regards,

    Perry


    Please remember to mark the replies as answers if they helped. If you have feedback for TechNet Subscriber Support, contact tnsf@microsoft.com.


    Click here to learn more. Visit the dedicated forum to share, explore and talk to experts about Microsoft Teams.

    Friday, March 22, 2019 5:39 AM
  • Hi Scott HD,

    Any updates? Can you send emails normally?

    Regards,

    Perry


    Please remember to mark the replies as answers if they helped. If you have feedback for TechNet Subscriber Support, contact tnsf@microsoft.com.


    Click here to learn more. Visit the dedicated forum to share, explore and talk to experts about Microsoft Teams.

    Monday, March 25, 2019 8:53 AM