Hi Jeff Tresnak,
When issue occurs on Outlook, have you tried sending these message on OWA to see if it works normally?
Are there any error messages when you send the message?
We can also try recreating the send/receive settings file (<profilename>.srs) in case the send/receive settings file is corrupt. To do this, exit Outlook, navigate to the following path:
C:\Users\%username%\AppData\Roaming\Microsoft\Outlook
Find and rename the <profilename>.srs to <profilename>.old, then, restart Outlook and test the issue again.
If it doesn't help, we could
create a new profile to check the result.
Any updates, please feel free to post back.
Regards,
Perry
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