I ask because I suspect maybe newer versions of iTunes don't support them, but don't have an extra Mac to try an earlier version. I have a 3rd gen and a 4th gen iPod Classic that I stopped using a long time ago. One was a gift and the other I just didn't bring with me on the road. I'd like to use them now connected to my stereo (one in bedroom, one in living room). But neither will connect with my Mac. Why do they stop working? I understand if I used it all the time but shouldn't one hardly used still work?