iTunes Playlists Not Importing

I saw that you assisted another Plex Pass user. I have an issue and can’t seem to find anything on Plex Forums that helps. I am happy to pay you or someone else to help resolve my problem, which is as follows: Until recently, I kept my iTunes media files on my PC. Recently, I got a NAS and put all my iTunes media files on my NAS but kept my PC as my Plex Media Server. Even since I moved my iTunes files to my NAS, I have lost all of my iTunes playlists on Plex, both on my Plex Media Server and all the roku boxes from which I access my music. On both my Plex Media Server and all Roku boxes it shows the playlist but when you try to play them its says “There Are No Playable Items”. Please help. The main reason I use Plex is to play my iTunes playlists, and is not much use to me if I can’t access my playlists. Thanks in advance for any feedback. Thanks. Brad

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?

I soooo appreciate your response. When I moved all my media to the NAS, I changed my settings in iTunes to pull all the media from the NAS. iTunes is working perfectly and not having any issues with playlists.

How do I disable my playlists in Plex? There is no “…” next to Playlists on PMS to allow me to update, delete etc. There also isn’t the gear icon on the far upper right, that used to allow updating of playlists.

How do you save the library to XML? I don’t see that option on iTunes.

···
  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.

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

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

  3. 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).

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

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

  6. 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?


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When you create the library section, in the advanced tab, “Import from iTunes”

When I go to the library section, the “Advanced” tab remains faded so that I can’t choose it.

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I did not get an image. Only a white square.

Something else is up . I will need your logs.

Since this is now turning into more than a quick question, with your concurrence, I will move the regular forum and continue ?

Hold the phone. Now I see it. Should I just delete my existing music library from PMS and then just do a new music library with the import from iTunes checked?

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Just create a new library.
no need to delete the old one until you know you got it :slight_smile:

Got it. I’ll give it a try.

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Sure. That’s fine. I will try a new library and let you know the result. Be back in a bit. Thanks again. Really appreciate it.

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Well, it took until today for my new library to complete its scan, and still no playlists. I did check to import the playlists on this library. Thoughts? Advice?

Smart playlists aren’t supported. Only “simple” ones.
which type are you using?

Simple

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Then this needs to be moved to public for additional assistance. I can’t be of any further help with it as I no longer run windows. iTunes doesn’t exist for Linux

With your permission, move to public?

Sure. Thanks for trying. Its been frustrating.

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I am certain. This is why I stay in Linux. It’s predictable and stable.

I do not use Alexa. I had no issues until I moved my media files to a NAS. Once I did that, I lost all my iTunes playlists. I have imported xml files for each of my playlists to my music file on my NAS and have restarted my PMS. I have checked the box in setting up my music library on Plex to import from iTunes. None of this seems to work. Any thoughts would be appreciated. Thanks.

this may or may not apply to your specific problem, but in general problems with itunes import almost always caused by difference in file path.

if your itunes on a pc and your PMS on a nas/server (and the music is also on that server), then the paths will be different between the PC (music will be remote to the pc) and the server (music will be local to the server).

you can copy the itunes.xml to a linux server and import it successfully, however you will probably need to manually correct every file path so that it is a local path and not a network path.

depending on the size of your library/xml file, you will need a file editor that can open that xml and do a search/replace.

TLDR;
when itunes and PMS are on same machine, itunes import should work automagically.

when itunes and PMS are DIFFERENT machines, path differences cause problems and nothing imports because itunes see one path, while PMS uses a different path.

Thanks. My media files are on a NAS and both PMS and itunes are on my PC. Any thoughts?