See if this works..I've recently had similar problems with my first iPod..Something was not going right & I could not download the wav files or something,i don't remember..Anyway..Get a blank re-writable disc.Download all your music to discs.Then Re-uplaod them through the iTunes part that goes with the iPod.I had to rename all the titles/artists,but I was able to hear them with my iPod!! Hope it helps..