Here's my scenario... Old Computer = HP, Win 7, 64 bit New Computer = 21.5" iMac, Bootcamp, Win 7, 64 bit Old iTunes library was maintained on external hard drive. New iTunes library was created by directing new iTunes to external drive and copying old iTunes library preferences file. New iTunes is set up exactly how old iTunes was. Playlists, play counts, etc... Here's my problem... When I try and sync 160GB iPod Classic to new iTunes it wants to erase iPod and re upload the entire library. I would like to avoid this if at all possible, not because I have missing data but because I don't want to take the time to do it. 80GB of music equals long time transferring files. If I can't accomplish this then I guess I have no choice but I thought I would ask anyway. Please advise. Thanks.