Won't Sync Protected AAC Audio Files

We've got a 2nd gen shuffle that won't sync protected AAC audio files. The background story is that my hard drive fried and I had to rewrite it. I've reset the shuffle and now we're trying to put brand new music on it. It will sync the song that is labeled "purchased AAC audio file." Fact of the matter is, we purchased all of them!
Any ideas? Any help will be most appreciated.

1. Try playing one of the songs that won't sync in iTunes then try to sync them again.
2. If that doesn't work, go to the Store menu at the top in iTunes, Deauthorize your computer then play one of the songs you purchased. When prompted enter your Apple ID and password, then Resync.

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