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[reddragon105]

I've got a classic 80gb Ipod video that currently has about 1500 songs on it (taking up just a tiny fraction of its capacity).

I'm trying to use it with my 360 to listen to my own music as I'm playing. I've just connected the Ipod, selected it in 'Music Sources', clicked 'Play All' and put it on Shuffle. Simple enough, I thought, except it's not playing through all of the songs - it's playing the same songs over and over again, it's shuffling, but only through the first 100 or so songs (which takes me to songs starting 'Ba' and no further). I can play songs further down the alphabet by directly selecting them, but of course then it just plays the one song over and over again.

Any one else had this problem? Is it a common issue? How can I fix it?