When a song will not play on your iPod, make sure that the files are in a format that is supported by iPod.
You may also want to try de-authorizing and reauthorizing your computer.
Apple say "After you've de-authorized and reauthorized your computer, open iTunes, select your iPod, and choose Update iPod from the File menu. If that doesn't resolve the issue, try restoring your iPod.
"After you've restored your iPod, open iTunes, select your iPod, and choose Update iPod from the File menu. If that doesn't resolve the issue, try recreating your iTunes library.
"After you've recreated your iTunes library, open iTunes, select your iPod, and choose Update iPod from the File menu."
Apple also says:
"If none of the above steps resolved your issue, there may be an issue with the music files. If you have a backup of the affected song files, delete the files from your iTunes library and then add them back in from your backup. If you haven't been keeping a backup of your purchased music, you can find out how to do this here.
"If the affected files came from an audio CD, try importing them into iTunes again from the disc. After you've replaced the affected files with copies from your backup or CD import, open iTunes, select your iPod, and choose Update iPod from the File menu."Index
- When songs won't play
- Warning about Windows DRM and the iPod
- Using Apple's Disk Utility, other disk tools to solve iPod directory/permissions problems
- USB 2.0 synchronization/data transfer problems
- Audio dropouts, pauses
- Revitalizing a frozen/unresponsive iPod
- Sudden, Unexpected Resets
- Repair difficult, replacement often cheaper: Cracked LCD screens and more
- Quirkiness when synchronizing with high-power USB 1.1 ports
- Mac freezes when going to sleep with iPod connected
- iTunes-purchased tracks won't transfer to iPod
- iTunes crash on iPod connection; solutions
- iSight interference
- Falling Asleep (appearing off) suddenly
- iPod-stored tracks cannot use some iTunes features
- Updater software issues
- Shuffle USB connectivity issues
- Remote Control problems
- iPod not showing up in iTunes
- Batteries: Charging, maintaining capacity, maximizing life; more
- Preferences not sticking
- Extracting files from an iPod to a Mac
- Distorted/static sound
- Dealing with Smart Playlists
- AppleCare for iPods
- Complaints about Apple earbud quality; alternatives
- Data loss -- Music disappears from iPod