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APNS Certificate Request for OUtlook

I have a user using outlook 2007 and we have exchange 2010.  Something happened to his machine that is now requiring him for an APNS certificate every time he opens outlook.  It is not connecting to exchange and cannot enter a username and password.  Has anyone seen this or know what to do?
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I think he got hit with a virus or something as his machine will not even load up now.  I am just doing a wipe of his system.  I appreciate all your help though.