Sent items missing from Outlook sent items folder

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Sent items missing from Outlook sent items folder

Randy Greig 1

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Answer 1

JeffYang-MSFT 6,261 Moderator

Hi @Randy Greig ,

Welcome!

In order to better understand and solve your issue, I am trying to retell your issue here: When sending two email messages to another user in the same domain, only one email would be saved in Outlook sent items, even checking from your web mail, right? If this is your case, please continue:

Do these two sent email messages have any other characteristics aside from the same recipient? What if try sending other two normal plain text emails?
Is this an issue that only happens when sending emails from Outlook desktop client? It is suggested for you to try editing and sending email from your web mail and see if the issue has any difference there.
By the way, does this issue only happen to this specific user? Do other users in your organization have the same issue?

As I know, Outlook rules can lead similar issues. Please try to uncheck all the Outlook rules you have to temporarily disable them via Home > Move > Rules > Manage Rules and Alerts, click OK and restart your Outlook to see if the issue could be resolved.

Any update about this issue, please feel free to post back.

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Randy Greig 1 Reputation point

2021-04-26T14:24:30.897+00:00

Hello @JeffYang-MSFT

No other user has experienced this issue. I believe that the issue is related to the fact that both of these emails were in the Outlook outgoing email queue when the user shutdown her laptop.

I did a message trace and both emails show as having been sent and delivered. The email that is missing from the sending user Sent Items folder were received because the receiving user replied to the email.

The user and myself are concerned that the email is missing from all folders (outlook and OWA) for the sending user account.
JeffYang-MSFT 6,261 Reputation points Moderator

2021-04-30T08:58:44.007+00:00

Hi @Randy Greig ,
Thanks for your reply and update.
Is this an ongoing problem even still now? Can you still reproduce this issue again when sending two similar emails from your Outlook client?
Randy Greig 1 Reputation point

2021-04-30T13:22:46.737+00:00

@JeffYang-MSFT ,
No, the problem has not happened again.

I believe that the problem was caused but shutting down Outlook before the messages were fully sent (they did go out).

Exchange sent them, but did not flag them as sent emails in the mailbox. They were removed from Outlook Outbox, but not updated/entered into Outlook Sent Items folder.
JeffYang-MSFT 6,261 Reputation points Moderator

2021-05-04T09:20:05.173+00:00

Hi @Randy Greig ,
Thanks for your reply again.
Well, what I can thought of is that we could try the Search-Mailbox cmdlet to search this specific message and see if we could find it. If it still fails, I'm afraid that it might not be able to recover.

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Sent items missing from Outlook sent items folder

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