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One of our users is no longer able to see any mail in his "Sent Items" folder. When he sends out a message it sits in the Outbox until he manually selects "Send/Receive" from the menu. I checked the Outlook Admin Center and confirmed the messages are sending, but they do not appear under "Sent Items" on Desktop, Mobile (iOS), or Online.

I did confirm that he has the app configured to save sent mail, and his Windows edition does not have group policy settings. Microsoft says the Exchange service is up and no other users have reported an issue.

Can anyone provide guidance as to where I should look next?

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    Can anyone provide guidance as to where I should look next? - Open a support case with Office 365. It's free of charge. – joeqwerty Apr 1 at 17:18
  • Fair enough. I ended up doing that anyway. Thanks, Joe – user626073 Apr 1 at 19:26
  • Hi, please check if the below answer is helpful to you, if your problem has been fixed, you could mark the best answer or share your solutions so that others with the same question could find it. Have a good day! – Ivan_Wang Apr 7 at 2:12
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The following questions are to narrow down your problem:

  1. What's the version of your Exchange? Exchange Online or on-prem Exchange server?

  2. Did you encounter the mail flow issue when sending emails to internal/external email addresses?

  3. Did you fail to send emails only when using Outlook desktop?

  4. Do you also encounter the same issue when sending emails via OWA/Outlook for mobile device(Outlook on the web)?

  5. Did other users(mailboxes) encounter the same issue?

If OWA/Outlook for mobile works fine, the issue may be caused by clients themselves, try to run Outlook in safe mode or recreate the profile of this mailbox and see if there is any difference.

On clients, check if there is any delay delivery setting configured. For example, the Delay Delivery setting on Outlook desktop:

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If you are using on-prem Exchange server, please check if all required services are running, make sure the five default receive connectors are existing and there is an Internet mail Send connectors.

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