i plug it in and get the ipod not supported check owners manual error, this is a 4gen ipod i wonder if its too old, but the software...?? do you auto update your ipod from apple when it synchs with itunes, because that would mean you had v 3.1.1... i think, when you open the ipod startup and go to settings or about it will give you the version its running, at least thats what im looking at and mine says 3.1.1