Sounds as if the iPod Compatibility settings have not been enabled. Go to Tools | Options | Portable Audio Devices | iPod and click 'Configure'. Then click 'Device Configuration' and enabled the iPod Compatibility settings.

Let me know if this solves the problem.

-Rusty

Is there a known sync problem with a nano so that when you play the songs several scan for about a second then it stops on about every 5 or 6th song to play it. When you go to the next song the same thing happens.