Ipod cannot be updated (-50 error) when trying to upload album art

For some reason, when I check the "Display album artwork on your ipod" box, I'll end up with an -50 error, even though the album art is already in iTunes and I can upload songs/photos/videos just fine. Latest version of iTunes and iPod FW.
I've tried unchecking/rechecking the box, ejecting the ipod, restarting the ipod, itunes, Windows, to no avail. Hoping it's just an annoying problem with a simple solution.

disconnect your ipod without ejecting it using itunes. just unplug it, and all the artwork should be there

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