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Solution:  I have a number of users with large mailboxes, and whenever mailboxes get large Outlook seems to get flaky.  On Monday a user with one of these large mailboxes approached me and said that every time he sends an email the recipient gets 2 copies.

After I did a bit of research, here is what I did to resolve the issue:

  1. I did a full reinstall of Microsoft Office.
  2. I did a repair of Microsoft Office.
  3. I read that having a too many items in the sent folder can cause this issue, so I archived items from his sent folder into a separate .pst.  I suppose you could also delete unneeded sent items.
  4. After the users sent folder was reduced Outlook only sends 1 email.
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