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Outlook 2019 OEM/OWA Exchange 2016 on-premise not saving all email to Sent Items

At the moment I have reports of two users that intermittently have emails stuck in their Outbox. When they noticed and get the emails sent the messages are not always saved to the Sent Items folder. Even when I check in OWA only some are in sent items. I confirmed the emails were sent through our 3rd party cloud filtering portal

One user also reports auto-complete does not work too around the time of the issue occurring. I can't see any stand out event logs errors that could cause this.

I could re-create their Outlook profile but why would the messages be sent but not saved to Sent Items even in OWA?

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Jazz Marie Kaur
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  • What version of Office or Outlook is being used? Can you describe the environment a bit further, OS, and Exchange servers? Are the users remote or onsite or in different locations.
Take a look at fellow Expert Andrew Leniart's troubleshooting tip article:
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Thanks for the links and advice

Office Home and Business 2019
Exchange is on Windows Server 2016
Exchange is Exchange Server 2016 CU20

I know of three affected users now so there could potentially be more.

It's similar to this post on Spiceworks, especially the post from June:


I will update here if I resolve the issue
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Saif Shaikh
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if it is mailbox specific try to run the new-mailboxrepairrequest online tool from EMS on exchange server.

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Thanks Saif, I will prepare to try this command if the Outlook client troubleshooting fails.

New-MailboxRepairRequest -Mailbox user@domain.com -CorruptionType FolderView

This should repair and folder view inconsistencies but will take a long time to run

This could be done to check all:
New-MailboxRepairRequest -Mailbox user -CorruptionType ProvisionedFolder,SearchFolder,AggregateCounts,Folderview

I tested sending an email to myself from OWA and that was successfully saved to sent items. Earlier when the user had emailed me from Outlook I received the email but it wasn't saved to Sent Items when I looked in OWA.

I feel it is more Outlook/workstation related than Server but that depends on workstation troubleshooting results.
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We have a suspicion that this might be the cause and it will be investigated with the end users next week

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Exchange is the server side of a collaborative application product that is part of the Microsoft Server infrastructure. Exchange's major features include email, calendaring, contacts and tasks, support for mobile and web-based access to information, and support for data storage.

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