Computer Authorization
Why do have to keep authorizing the computer and it still doesn't allow songs to play?
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If you see repeated requests to authorise your computer for a song, or songs, that you have purchased from the iTunes Store, that suggests that the song file did not download correctly; i.e. the file is either faulty or incomplete.
In that event, delete the song and download it again. Make sure that you click on show All purchases, in order to see everything.