Maxroby,
Have you tried deleting them from the ipod then emptying your trashcan? This 
works for me. I'm using a 2nd gen nano... not sure if that matters though.

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[feisty] deleting a song from the ipod only updates the database
https://bugs.launchpad.net/bugs/96669
You received this bug notification because you are a member of Ubuntu
Desktop Bugs, which is a bug contact for rhythmbox in ubuntu.

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