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

• 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:

•  Troubleshoot and Fix Outlook Problems | Experts Exchange.
• If its both OWA and Outlook could be a server-side problem, but its just 2 users so far -  examining the log files may help you if more report issues, could be a connectivity problem
• Are they on the same OS and versions of Office and Windows compared against non issue users?
• Try the Microsoft SaRa Diagnostic tool also:
  • https://docs.microsoft.com/en-us/outlook/troubleshoot/performance/how-to-scan-outlook-by-using-microsoft-support-and-recovery-assistant

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:

https://community.spiceworks.com/topic/2314781-outlook-not-putting-copy-of-email-in-sent-folder

I will update here if I resolve the issue

if it is mailbox specific try to run the new-mailboxrepairrequest online tool from EMS on exchange server.
https://docs.microsoft.com/en-us/powershell/module/exchange/new-mailboxrepairrequest?view=exchange-ps

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.

We have a suspicion that this might be the cause and it will be investigated with the end users next week

https://www.ahead4.com/news/outlook-sent-items-bug