Can't Update File in Use

When ever I connect an iPod I get the message that the iPod can not be updated because the "file" is in use. How do I eliminate this proble? Thanks.
iMac   Mac OS X (10.4.8)  

I have the same problem. I have a feeling it might have something to do with the "Manually manage music". But maybe not. I'll keep looking. I'll let you know if I find anything.
iBook G4   Mac OS X (10.4.6)   iPod pictures 20GB

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