Steps to reproduce.

  • Turn off importing of tracks to iTunes Library
  • Import Tracks
  • Create playlists
  • Change file names or move files
  • Have broken playlists

I understand why this happens. It's because of the nature of linked files. Is there any way to have the playlists maintain integrity or fix them? It seems even when I use iCloud music the playists are "brittle" and can easily break.

  • Hi Andrew, welcome to Ask Different! :) Can you please clarify your 4th bullet point? Where are you changing file names or moving files? Within iTunes? On a Mac/PC? – Monomeeth Aug 8 '17 at 1:17
  • Say I have a file on Windows (not that the OS matters) such as C:\music\sick_single 5A - 120.mp3 and I rename it to C:\music\sick_single Cm - 120.mp3. If it is on a playlist in iTunes it no longer is technically existing in accordance of how it was added to that playlist. So the play list is rendered broken. – Andrew Mortimer Aug 8 '17 at 18:53

The best way to preserve your playlists is to manage them, as far as possible, within iTunes.

It seems to me from your question and comment that the biggest issue arises when you rename a file you've previously added to a playlist. However, instead of renaming the file within your operating system, you should do it within iTunes. One way to do this is:

  1. Within iTunes right-click on the song
  2. From the context menu that appears, select Get Info (or Info)
  3. This brings up all of the metadata for the song, including the field for its name
  4. Rename the song
  5. Click OK

Managing all of this via iTunes will ensure you don't break your playlists.

Also, you may want to check your advanced settings within iTunes and play with the Keep iTunes Media folder organized and Copy files to the iTunes Media folder when adding to library options to determine what works best for you.

  • That would be ideal on a per track basis but does not scale. Especially if you have other programs editing meta data and file names. I think I may just need to have redundant file systems. One where iTunes "owns" the files and one where the other programs "own" the files. I was trying to not have to do this, but it may be the only solution. :( – Andrew Mortimer Aug 9 '17 at 12:42

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