The only way I've been able to upload playlist to my iPod without duplicating files is to eliminate the files that will be in the playlist from the iPod first, then upload the playlist songs and all. It sucks, but that's how I do it. What I've resorted to, is allowing duplicates to exist on the iPod so I can have the same song exist in multiple playlists. The Music Match software is a Joke (capital "J"). I can't figure out how you're really meant to use it. At this point, I think it's software isn't very well thought out. Maybe if I wasn't familiar with Emplode, it would be easier to get along with the Music Match stuff but I doubt it.