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I have a folder of music that gets updated from time to time. It's outside of the iTunes ecosystem. By that I mean it's not being managed by iTunes, not do I add new music to the iTunes library.

I would like to have the new music in this folder automatically added to an iTunes playlist so I can sync it to my iPod.

I cant use the "Automatically Add to iTunes" folder as that seems to create a copy of the music in the iTunes folder. I just want it to be added to the library.

Ideally I will be able to use a smart playlist to sync the newest 25 tracks (without having to even add the files to the library). But I don't think smart playlists work on non library files.

Is it possible to sync music in a folder to my iPod in this way, either by automating adding it to the library, or having the smart playlist reference the folder directly?

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Prefs > Advanced - uncheck "Copy files to iTunes Media folder when adding to library" - then you should be able to use the "Automatically Add to iTunes" folder without it making duplicates.
Though, once you shift to that method, it's up to you to keep track of where the files are.

[untested... it may need "Keep iTunes Media folder organised" to be unchecked too - try it with & without]

  • Ah thanks, although still a manual process to keep the database up to date. I guess I could use a third party backup software like syncback to send files over, but I don't know how it would compare the directories as it isn't really a conventional folder with a file list. – square_eyes Sep 28 '14 at 6:46
  • Hmm, also files still seem to be copied to my iTunes folder when using the "Add to iTunes" special folder. So I'm back to the drawing board. I think the setting you mention only works for dragging and dropping on to the actual app. – square_eyes Sep 28 '14 at 7:03
  • Hmm.. either way, iTunes doesn't like to not be able to find files it thinks are still there; so a better [read 'more tedious'] method might be to let it do its own thing, then go back into the main songs window & delete tracks you've finished with. That would keep iTunes happier... if not you >.< – Tetsujin Sep 28 '14 at 7:06

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