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Originally Posted by Kewl X5
Who knows, but I think the iTunes and iPod software for Windows is a little buggy IMHO......Apple is trying to get you to buy a Mac... 
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No doubt it is. I did manage to get the iPod to sync with iTunes 5.0.1.4 after rolling back the Updater version. It took a while for the iPod to sync all of the iTunes library but it worked. I hate technology but I love technology. It's very frustrating sometimes.