[Simon]

Hiya Jay,

I've never had that problem. Doesn't seem like it should be doing that though, except maybe with some copy-protected songs purchased online, but that shouldn't be the case with all the songs you copied from CDs yourself.

Only two things I can think of on my first cup of coffee. One would be to check that your backup copies of the songs are really saved in the formats you think they are. The other, if you haven't tried it already, would be to copy a few songs from your external drive to your internal drive and then try loading them to the iPod from there to see if there's any difference in your results.

Okay, third thing, and maybe the best idea. You just bought the iPod so why not call Apple support? You should a 90 day free support window even if you didn't get the Apple Care plan.