I have the same problem on Ubuntu 10.10. It seems that Rhythmbox
transfers the files but somehow "loses" the .mp3 extension in the
process. The files themselves are not damaged, because they work fine if
I transfer them on the ipod using itunes on windows after re-adding the
extension manually.

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rhythmbox adding songs to ipod no sound
https://bugs.launchpad.net/bugs/190818
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