Itunes will not update ipod

I have added a large amount of music ti itunes, but every time i try and update this onto my ipod i get an error message from itunes. unknown error(-69). has anyone had this before, if so what can I do. I have restored ipod to factory setting but still have the same problem. I have reduced the amount of songs I try and transfer, still the same.
could this be to do with he new itunes what can i do????

hi Aubrey!
i will have my itunes up. then plug in my ipod and it says updating ipod but when it says it is okay to disconnect still my ipod has 118 songs while my library has 176
hmmm. if Katie's suggestion about the ipod updater software doesn't pan out (it's certainly worth checking), maybe try investigating this possibility:
http://docs.info.apple.com/article.html?artnum=93499
love, b

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