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Helpful answers
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Dec 13, 2012 6:44 AM in response to kaberridgeby lllaass,Only the 4G and later iPod will play HD movies. Try redownloaing the SB version and then sync that to the iPOd.
Downloading past purchases from the App Store, iBookstore, and iTunes Store
Also see:
iTunes: May be unable to transfer videos to iPhone, iPad, or iPod
iTunes: Frequently asked questions about viewing and syncing videos