itunes and apple never let you take songs off an ipod and put them on your laptop, there used to be an open source program I think called u shuffle, or shuffle pod, or something like that, that I used to do it but it doesn't work anymore. I guess because apple wants you to pay money to their itunes store whereas I had gotten tons of mp3s downloading them from bit torrent. I learned this hard way, going to just add songs, it does the sync and then wipes everything, you can only have songs that are already in your itunes library on the ipod