iTunes Playlists Not Importing

First, I help because I enjoy it.

Secondly, (longer answer here haha) and it’s been a while since I’ve even done this.

  1. I am not a Windows expert but know enough I hope for your issue
    2 Itunes keeps the absolute path, which was originally on the local machine, for each of your files.

  2. Playlists imported from iTunes are simple playlists (this is where the pathname comes into play

  3. When you moved them to the NAS, they no longer exist where iTunes is expecting them

  4. iTunes must first be made aware of where the files are now. IIRC, you *add the new location folders to your iTunes library and it will self update those locations (like Plex finding media after you move it).

  5. Once iTunes is aware, you can disable your playlists in plex (erases them) then re-import them back.

  6. Plex will see the location has changed for each song on each playlist and update where it knows the file to be.

  7. With Plex updated, normal operation returns.

To verify this, I strongly recommend a small test case… Perhaps copy out an album into a new folder somewhere and add just it. See what happens. If the playlists there update, you’re good.

Something else I remember doing … maybe the TL;DR of what I said above

  1. I had iTunes update to the new locations on the NAS (added those folders)
  2. Had it save the libary to XML (this somehow seems really important)
  3. Have PMS import that updated XML again. (this is the turn off/turn on step)

Does this make sense in any way?