I upgraded from a nano to a 5th gen 30gb video today and they music is not playing through the headphone socket... I've got an iTrip and it works through there. Any suggestions why this could be?! Thanks, Matt.
Also the hold button switch is not working either, I bough the iPod off eBay and it came today. Brand new and sealed. I put a message down to apple and their telling me that my warranty has expired, although im sure its the 5.5gen ipod video cuz its got the brightness option on there... Any suggestions on what to do?!
Brightness option was a firmware upgrade. Since the warranty is expired it probably is a regular 5th gen, the standard warranty is 12 months. Try restoring your iPod, if that doesn't work it sounds like you bought a bad iPod, might want to talk to ebay about that.