I have a 30GB classic that will connect to the mac and you can play off the classic. The headphone jack stopped working so I was then using it on Bose SoundDock and it was fine. Now the ipod shows it’s playing but there’s nothing coming through the Bose and while using the Bose remote you can see when you pause/play/forward and back are working so the Bose is talking to the Classic but there’s no sound. I pulled out my other classic a 160GB and it’s the same size and it played fine. I don’t know where to go from here. I have an entire audio library that without some 3rd party software I can’t retrieve off back into itunes. I’ve checked the port and made sure there were no rogue lint balls or other debris and still nothing. My endgame is for it work on the Bose Sound Dock. Any suggestions, tips, or tricks would be greatly appreciated.