Playlists don't sync to my iPod Classic

This could be a matter of ruling out every other possibility. I wonder what has changed?

The most likely thing is that the Sync options have changed.

With the iPod connected to iTunes, make sure that the sync options are still set the way you want them to be:

1. Look on the device/Settings/Summary pane and make sure that Manually manage music and videos is not turned on (not checked), as shown in the screenshot:
2. Note whether you have Sync only ticked songs and videos turned on. If it is, make sure (in the Library) that the songs in your Playlist are ticked as well. Notice in the screenshot that we are now looking in the Library, not on the iPod:
3. Now back with the iPod:
   1. check the device/Settings/Music pane (1.):
   2. Is the Sync Music (2.) still on (selected)?
   3. If you have chosen Selected playlists, artists, albums and genres (3.), have you also selected the specific playlists in panel 4., because if the specific Playlists are not ticked (not selected), they will not be added to the iPod. Note though, that if you have chosen Entire music library (3.), the panels (4.) will not be displayed and the Playlists will (or should be) added to the iPod as part of the Entire music library

I realise this has become a complicated set of steps, but I cannot think why else this should not be working.

If you still have not resolved this, the next obvious things to check are:

• if you have new songs in your iTunes Library, are they being added to the iPod, as they should be?
• are any other changes you make in the Library (ratings, song or album titles, artist name, changing the genre) being synchronised with the iPod?
• if you create playlists on the iPod (On-The-Go Playlists), they should be copied from the iPod to your iTunes Library by a Sync. Can you find them in the Library?*
  • if the On-The-Go Playlist is saved on the iPod, it gets named as "Saved 1" (if I remember correctly)
  • if you have an unsaved On-The-Go playlist on your iPod, it is named "On-The-Go" (again, if I recall correctly - my iPod Classic no longer works)
  • when On-The-Go playlists are copied into your iTunes Library, they should get renamed in the Library as On-The-Go x, where "x" is the next number available. They are Regular Playlists, so are listed (in the Library) below the Smart Playlists
  • On-The-Go Playlists are added back to the iPod under their new name*

Any joy?

If not, the only other suggestion I have at this time is to Restore the iPod. The Restore button is on the device/Settings/Summary pane. Be aware that a Restore will remove everything from the iPod and can only put back what is in your Library. If you have a large Library, you may need to split up the Sync into manageable chunks in order for it to be successful. The best way to do that is to use Sync selected playlists, artists, albums and genres (as mentioned above), but making sure that you eventually include everything you want. So, sync a few playlists etc. and once the sync has competed, select a few more playlists etc. and sync again.

* Additional text added by author after initial posting.

1. Have you been able to Sync the Playlists to this iPod in the past?
2. Did you create the Playlists (in your iTunes Library) before connecting the iPod to the Library?
3. Can you see in the menu item Playlists on the iPod?
4. Is that Playlists menu empty when you look into it?