Try this. Send the user an email with a specific word in the subject, make it unique. Have the user reply to it, then do a search for that unique word to find out where the email is located.
I'm Certifiable, not certified.
It just means my answers are from experience, not a book.
Sometimes this happens if that user is accessing emails at two different workstations at the same time. In the case Outlook is probably being accessed by two people.
There could be a security breach, in my case it was!
Change users password, log off, and log in to see if problem persists.
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