When you plug your ipod in and you click cancel to syncing your songs, Click your ipod in the left hand column. It should show you that your ipod is up to date, give you the option to restore your ipod to factory settings and under that it has the option to sync your library when you plug it in. Or you can manually control your library. click that if it isn't clicked already. Then just drag the songs you want added to your library. Should work
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