Here's something to try: http://support.apple.com/kb/HT1320

This worked for me. I followed the reset instructions with my iPod
plugged in. The screen dimmed, displayed a do not disconnect message,
and within thirty seconds the system recognized and mounted the device,
asking me what application to associate it with. Music was not lost.

iPod Nano 2nd generation, model A1199
also posted here: http://ubuntuforums.org/showthread.php?p=9523892

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Does not detect hotplugged ipod shuffle
https://bugs.launchpad.net/bugs/578194
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