I have a 64GB 'pad and I've noticed several dupe tracks on it, but when I connect to iTunes the "show duplicate items" choice is greyed out; I guess it only works for the iTunes library itself and not for devices. As an experiment I tried intentionally adding dupe tracks and it let me add any # of copies I wanted to the 'pad. That's crazy! Is there some option to disallow or alert you to multiple copies (like when you try to copy a dupe file to a folder) or at least show them? I have more than 64GB of music so I manually manage the content. To be absolutely clear: I have NO duplicate tracks in my iTunes Library, I have an unknown # of duplicate tracks spread through various playlists on my iPad. Each playlist shouldn't need it's own copy of the file, right?