Make sure you have you user's manual. If you don't have it, go to Apple website.
Make sure the songs you are trying to add are in the format suggested in the user's manual - warning: WMA files are trouble for reasons I don't feel like explaining anymore.
If they are, then make sure that you still have enough memory left in this player.
If you do have enough memory, follow Apple's 5 R's:
These are for Nano, but they apply to all iPods:
Reset, Retry, Restart, Reinstall, Restore
Remember these five basic suggestions if you have a problem with your iPod nano. If
one of the following doesn’t help, read on for solutions to specific problems.
â Reset your iPod nano. See “General Suggestions,” below.
â Retry with a different USB port if you cannot see iPod nano in iTunes.
â Restart your computer and make sure you have the latest software updates
installed.
â Reinstall iPod and iTunes software from the latest versions on the web.
â Restore your iPod nano. See “Updating and Restoring iPod Software” on page whatever.
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