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Every time I remove a song from a playlist on PC, then sync to iPhone via iTunes, the playlist is updated (i.e. it doesn't include the removed song), but the song is still in the library. That adds up over time. Now a bunch of "rogue" songs have accumulated that aren't in any playlists that take up quite a bit of storage. Any way to get rid of them?

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    Please ask only one question per question. – nohillside Jun 9 '20 at 7:10
  • Do you want to get rid of those songs only on the iPhone, or also remove them from your Library as such? – nohillside Jun 9 '20 at 7:11
  • Only the iPhone. I think I've figured it out. I set up a smart playlist that has all the songs that aren't in any existing playlists. Then I dragged the playlist onto the iPhone, selected all the songs in it and pressed shift-delete (right-click -> delete from library didn't seem to work). That's still pretty cumbersome (having to add every playlist to the smart playlist manually), but that's faster and less error-prone than removing one-by-one. – stackexchange_account1111 Jun 9 '20 at 7:35
  • Please post this as an answer and accept it then. – nohillside Jun 9 '20 at 7:47
  • Done. I am still interested in a more streamlined solution, so I don't want to accept it just yet. – stackexchange_account1111 Jun 9 '20 at 8:01
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How about only syncing the playlists you want instead of the entire library in iTunes (or Finder if your computer is macOS based)?

If you are someone that learned to drive a car without an automatic transmission, your method is akin to manual shifting. You could also enable Apple Music or iTunes Match and then you no longer have to micro-manage which I played songs get removed as your device keeps track and cleans automatically when you run low on free space on device.

  • I am confused. I am definitely not syncing the entire library and only individual playlists. – stackexchange_account1111 Nov 9 '20 at 3:42
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Set up a smart playlist that has all the songs that aren't in any existing playlists. Rules:

Check Match music for all..

Playlist is not <Playlist name>

Playlist is not <Playlist name>

...

Check Live updating

Then drag the playlist onto the iPhone, select all the songs in it and press shift-delete (right-click -> delete from library didn't seem to work).

That's still pretty cumbersome (having to add every playlist to the smart playlist manually), so I'm open for other answers. However, this is faster and less error-prone than removing one-by-one.

  • If there are more than a few playlists that smart playlist will have a LOT of rules. – Pedro Dec 6 '20 at 11:09
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    You're right, I have something like 30 now. Have to redo the rule for every playlist that gets updated too. – stackexchange_account1111 Dec 8 '20 at 2:54

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