Can't copy (sync) music from Mac to ipod classic

When I attach my ipod classic (80gb) to my Mac Book Pro, it shows up in finder and in itunes. When I try to add a song to ipod, itunes says "Copying 1 of 1..."etc in the top center task bar of itunes. But then it's like it gets stuck. Normally it copies in 2 or 3 seconds, but it will look like it's trying to copy, then the ipod will disappear from Finder and itunes, and then I get an error message saying that the ipod was not ejected properly. Yet my ipod still says "Connected". Then I get an error message saying that it's corrupted and to try restoring it. I can still play what is on it, I just can't add anything else to it.
Given all of the other problems I'm seeing on these threads, I'm wondering if this had anything to do with the recent itunes update?

This sounds like an interesting snag - clearly if you can get copied CD tracks onto the iPod there isn't an issue PC to iPod.
I wonder if the inability to copy downloaded music is related to the very clever stuff Apple do to prevent you writing more than seven copies of those tracks? Just a thought - I have no idea how it all works, but it occurs to me it could get embroiled in network stuff?? If you are friendly with your administrator ask them if you can have a go at connecting your iPod to a computer with admin rights, and see if you get a more helpful error message.

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