Thanks to Troy at Smalldog Electronics‘ Tech Tails email newsletter for sharing the five things that you need to do if your musical friend is unhappy: 1. Reset your iPod.
2. Retry with a different USB port.
3. Restart your computer.
4. Reinstall iPod and iTunes software.
5. Restore your iPod
If these don’t work its time to call in the professionals or send it back to Apple under warranty.