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Aug 23, 2014 9:49 AM in response to BrianChemby joe_73,★HelpfulHi BrianChem,
Welcome to the Apple Support Communities!
I know it can be very frustrating when you are having issues syncing contacts. In your situation I would recommend using the attached article for troubleshooting this situation.
Troubleshooting Sync Services on Windows with Microsoft Outlook 2003, Outlook 2007, or Outlook 2010
http://support.apple.com/kb/TS2776
Have a great day,
Joe
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