Currently Being ModeratedJul 12, 2012 6:09 PM (in response to Kookie1030)
Which iPod shuffle model is it? This article about syncing the shuffle shows the four types.
As a test, you can try shutting down (powering off) and disconnecting all USB devices (including hub). Start it up with only standard keyboard and mouse connected (if it's not a laptop). Run iTunes. Connect shuffle to a direct USB port.