Environment: Outlook 2016 for Mac. Outlook 2016 for Windows on Windows 2016 Server using RDS. Problem: A message is sent from Outlook on the Mac and goes into the Sent folder on the Mac. The message is not really sent. Looking in Outlook for Windows on the RDS server shows the "sent" message in the Drafts folder. Opening OWA shows the message in the Drafts folder. If Outlook on the RDS server is not open, this problem does not occur.
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I'm here to narrow down the message issue:
- Did the emails which were sent from other accounts via Outlook for mac go into the Drafts folder?
- What's the version of your Exchange Server? Try to update the latest version of the app and send the emails again to check the result.
- Did you encounter the same issue when you sent emails via the build-in mail app? If the issue only happened on the Outlook for mac, maybe the issue was caused by the app itself, you could try to reinstall the app and re-add the account, then send emails again to see if the issue still exists.
Besides, here is one documentation which introduces the possible reasons and solutions of the sync issue, hope it helpful to you: https://www.nucleustechnologies.com/blog/fixed-outlook-for-mac-not-syncing-with-exchange-server/
Ivan_Wang
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