Unable to transfer library to ipod

this sounds simple enough. I have a 60G Ipod. I have already transferred about 5G onto it but now it will not work. It goes through the upload process but when I disconnect my ipod....my new music is not there. what is the problem?

I found this article "Some songs in your iTunes library aren't copied to your iPod" http://docs.info.apple.com/article.html?artnum=93867 maybe you'll find something in it, good luck.

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