Hi @WilliamM ,
A user in my organization will sometimes experience an issue where a sent email sitting in the Outbox for some time before it is finally sent.
For the message itself, did it have a large attachment? If so, it's normal to need more time to send it.
If the message is actually same with others, considering it could be sent finally , I think it may be caused by any performance issues on your Outlook for Mac, so what's the specific version of your Outlook (Outlook>About Outlook), please first ensure that you have updated to the latest version.
I noticed it's a new machine and you are syncing multiple messages from server, based on my research, I found a relevant thread that does mentioned it would slow the synchronization with the mail server and affect the client performance if there are multiple messages in Inbox, in this case, it's recommended to move the messages to your Mac machine. For more information, please refer to it : Mac Outlook slows down
Hope that would be helpful to you.
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