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was syncing offline playlists then it stopped

was syncing offline playlists then it stopped

I have an iPod touch and am using wifi I was downloading songs to be played offline and it was working fine for a good while then there was a song which couldn't be downloaded and then it messed up the offline option I can still download songs but cannot play them offline somebody please help...btw I have 35 more hours of the trial that was offered.
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