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Very strange. In my iTunes music library, in the "purchased" section, some songs will load easily using a drag and drop onto the Shuffle, while others, like the entire new Yo La Tengo album that I just bought, won't at all. I get the circle/slash symbol. Anyone know why this is and how to fix it?
Have you played the album on your computer yet? It's possible that if you recently updated iTunes and then downloaded the songs, that iTunes will want you to re-authorize your computer in order to listen to the songs.