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Outlook / Exchange Mail Stuck In Outbox

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Anyone know why someone's email would get suck in outbox running on Outlook / Exchange 2013 with Exchange showing as connected in status bar below?

User has periodic freezes (not repsonding) of Outlook then unfreezes. In this case it froze after pressing Send/Receive all and got the prompt to restart so we restarted outlook. Most messages in outbox were gone on restart and the last couple we watched dissapear from outbox, but none every appeared in Send box nor were the emails actually delivered.

Now wondering how to find the emails!

I posted this as in all my years I've never seen this behavior. User's PST file is over 22GB! That's huge! Thinking that may be part of the problem?

I'm not the Exchange specialist but is there somwhere on the server to look for emails that didn't get sent? My gut is it's a local problem and the emails never...


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