Hi still gettin to grips with my ipod so prob not the best advisor (sure some clever clogs will help you further!) but I do remember that my nano was playing up a bit so I restored the factory settings on i-tunes (when you plug i-pod in, it's the "button" on opening page so to speak). Though I did the mistake of deleting all of my songs by doing this (luckily i'd only imported from cds so didn't cost me anything!). so burn your tracks onto a disc first so if it wipes your i-pod as I think it will, you can re-install the songs. hope this helps