Every time I sync free space with songs it puts on about 80% of the same songs that were there before the sync. It has gotten so bad that I have gone as far as deleting songs that I have learned to hate because I hear them everyday without fail. I guess I've 'thinned the herd' of my music library this way. Library contains 8,000+ songs. Sync puts on ~400 songs. Roughly 5% of my music library is transferred in a sync. In the end only about 20 songs are different than before I sync'd. (If my math is wrong I apologize) Process I've been following: Music Library nothing is checked. Summary tab of my Ipod touch nothing is checked. Music tab the following is checked: Selected Playlists, Artists, albums and genres. Automatically fill free space with songs. I uncheck either or both of the above and sync to remove songs. Sync. Close Itunes Then remove my ipod touch from the base. (Tried rebooting Ipod at times here even) Reconnect. Open Itunes. Check the boxes and resync... same stuff put back on it. Any ideas?