motherland, music bought off itunes i believe is easy to transfer, of course I wouldn't know since I've never bought a song from them, my Itunes and ipod is all my cd's, I already had a huggggge collection of music before all this technology took off so I had no need to buy from them, anyway, music off cd's and other sources besides Itunes cannot be taken from your ipod onto your computer, I guess it's an anti-pirating measure, but as other have said before google itunes uploader or something like that and you should find a program.