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Feb 25, 2014 8:58 AM in response to Jon_Eby Allen A,Hello Jon_E,
There may be an issue with Sync Services transmitting information between Outlook and iTunes. The following article can help restore appropriate communication between the two.
Troubleshooting Sync Services on Windows with Microsoft Outlook 2003, Outlook 2007, or Outlook 2010
http://support.apple.com/kb/TS2776
Cheers,
Allen
