I get this problem too with my iPod touch 3G. I'm not sure it happens every 
time, but it's pretty often.
Sometimes I've unenabled the iPod plugin, restarted Rhythmbox, and enabled the 
plugin to get it working.
See this thread on the forums:
http://ubuntuforums.org/showthread.php?t=1467575

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Error when attempting to transfer music to iPhone 4
https://bugs.launchpad.net/bugs/630976
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