I sync my iPod touch with iMac, over 4,000 songs. Both are most current software. Most of the time I get SOME random duplicate playlists and sometimes it creates SMART Playlist 1, SMART Playlist 2, etc. Each with only a single random song in there. And sometimes it doesn't duplicate any folders or playlists. The song counts in the playlists are not always equal so I have to be careful and look at each one. Otherwise I would just "Delete From Library" the entire new and duplicate Playlist or folder. I am afraid of deleting songs from my library if I just blindly delete the duplicates. I hope this makes sense. Do I have a setting wrong somewhere?