Can't kill autofill email address

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Outlook version
Outlook 2010 32 bit
Email Account
Exchange Server
We recently migrated from on-premise Exchange 2007 to Office365 Exchange 2013.

One user cannot send email to another user with Outlook 2013 x86. When he types the email address or name in the To: box nothing shows up in the pop-up autofill box. But when he leaves the To: box the To: box changes to an email address for that user that hasn't worked in years. He can't delete that address from autofill because it isn't in the autofill box. He has that user in his contacts with the correct email address.

We figured out that if he types <real address> then the message gets sent to both the real address and the fake address, but that's pretty ugly.

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