Tested again today on an up to date system, same problem. Dragging a song to the iPod does nothing. I tried a file that needs transcoding (ogg) and one that would not (MP3), same result. It is a second generation Nano.
** Changed in: rhythmbox (Ubuntu)
Status: Needs Info => Confirmed
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Rhythmbox doesn't transfer music or podcast files to 2GB black iPod nano
https://launchpad.net/bugs/87514
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