I have a similar problem. While uploading music to an iPhone 3G the new
files are uploaded which can be seen in rhythmbox or any other music
player, but not by the iPhone-music-player itself. Already present files
also disappear from the  iPhone-music-player.

This behaviour can be reproduced on iOS 3.x and iOS 4.x on my iPhone 3G.

This problem can also be reproduced by other people regarding to
http://ubuntuforums.org/showthread.php?p=10222246#post10222246

The interesting thing is, that using banshee the sync works.

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https://bugs.launchpad.net/bugs/553301

Title:
  Music synced to iPod touch does not appear on device

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