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Outlook Exchange email disapearing

Last Modified: 2015-11-10
Not the first time this happens but always the same user:
He creates an email to send to a few people and sent it.

It gets stuck in his outbox... Still showing "Connected to Exchange"

He closes outlook and go back in it and the email is gone.... not showing in "Sent Item" and not showing also on my exchange 2003  Message Tracking Center...???
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