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Exchange 2013 - emails lost - after stuck in outbox

Got a user who reported items stuck in outbox. Had a look and they were getting send/receieve errors.

So, copied items from outbox into drafts and restarted outlook. Then copied back to outbox and resent each item manually.

Nothing in sent items and none of the users recieved. Its as if they disappeared. Done this before and its always worked ok.

Any ideas?
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Spencer Scherer
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Could they not send to anyone?  Was this internal or external mail?
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Nope all email was getting stuck. Sometimes restart of outlook fixed.

Weirdly I profiled up and could send the emails manually.
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Is the user using one mailbox or multiple mailboxes?
Multiple mailboxes. I think this may be part of the issue.
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Apologies for not commenting earlier.  Do you want to try something or are you happy with the solution you have found.
no other answers at all.