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Aug 10, 2014 12:22 PM in response to heelas.pby Jason L,Hi heelas.p,
Welcome to Apple Support Communities.
It sounds like there is an issue syncing with Outlook since updating iTunes. Take a look at the article below, it provides a lot of great tips that may be able to resolve the issue.
Troubleshooting Sync Services on Windows with Microsoft Outlook 2003, Outlook 2007, or Outlook 2010
http://support.apple.com/kb/TS2776
I hope this helps.
-Jason
