@cometdog: In the iPod's Sync menu, first disable syncing with all of
your playlists. Sync. Then re-enable syncing with all of your playlists
and sync again. That did it for me (Rhythmbox 2.96 on Ubuntu 12.04 and a
30GB 4th-gen iPod).

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https://bugs.launchpad.net/bugs/496681

Title:
  Rhythmbox does not save playlist on iPod

Status in The Rhythmbox Music Management Application:
  Fix Released
Status in “rhythmbox” package in Ubuntu:
  Triaged

Bug description:
  Binary package hint: rhythmbox

  this bug seems to be similar to bug #117925 which was set to 'Fix
  Released' in year 2008.

  1. playlist: when moving a file to the playlist which is already on
  the iPod I can see it there, but when syncing/ejecting the iPod it
  looses the playlist and it's content.

  2. copying a song/file from the musik folder via drag&drop directly to
  a iPod-playlist does not work at all. it looks like it works, because
  a + is on the icon but when checking the playlist no song is there. I
  would expect the song to be on the iPod and in the playlist where I
  draged it to.

  version: ubuntu 9.10,
  rhythmbox 0.12.5,
  8GB iPod (Model No: A1285 EMC No: 2287) listed in my ubuntu as ModelNumStr: 
xB745

  ProblemType: Bug
  Architecture: amd64
  Date: Mon Dec 14 20:53:20 2009
  DistroRelease: Ubuntu 9.10
  ExecutablePath: /usr/bin/rhythmbox
  InstallationMedia: Ubuntu 9.10 "Karmic Koala" - Release amd64 (20091027.1)
  Package: rhythmbox 0.12.5-0ubuntu5
  ProcEnviron:
   LANG=de_DE.UTF-8
   SHELL=/bin/bash
  ProcVersionSignature: Ubuntu 2.6.31-16.53-generic
  SourcePackage: rhythmbox
  Uname: Linux 2.6.31-16-generic x86_64

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