Unable to import ratings, play counts, playlists, etc. from iTunes library

After keeping an old Mac Mini alive well past its life expectancy, I’ve finally decided to take my music library out of iTunes and into Plex. I haven’t had any trouble getting the music itself and its embedded metadata into my library, but my understanding is that I should also be able to transfer iTunes-specific information like ratings, play counts, and playlists using the iTunes plugin. These are all things I absolutely can’t lose in this transition, but so far I haven’t had any luck.

I’m going to dump a lot of information here, probably more than even necessary, in hopes that someone will know exactly what I’m doing wrong.

Plex Server Hardware: Synology DS220+
Plex Server OS: DSM 7.1-42661 Update 1
Plex Server Version: 1.21.0-3744
Storage Configuration: I have two 3TB HDDs running RAID 1, represented as volume1. Inside volume1 I have a folder called MUSIC, inside which I pasted the full contents of the iTunes folder from my Mac. So inside /volume1/MUSIC we have the iTunes Music Library.xml file, folders called iTunes Music and Album Artwork, and a handful of other iTunes files.

Plex Server Settings: In the Settings menu, under Settings > Plugins on the left pane, I have the Enable iTunes plugin checkbox selected. For the iTunes library XML path field, I’ve tried all of these settings:

  • [blank]
  • /volume1/MUSIC/iTunes Music Library.xml
  • volume1/MUSIC/iTunes Music Library.xml
  • localhost/volume1/MUSIC/iTunes Music Library.xml

Whenever I change either of these settings, I open my NAS’ Package Center, stop the Plex plugin, and run it again.

XML File: When I first copied the files over to my NAS, each song within the iTunes XML file had a Location field which followed this pattern:
<key>Location</key><string>file:///Users/[my name]/Music/iTunes/iTunes%20Music/[artist]/[album]/[song]</string>
I ran a replace-all command on the file to change each path to this pattern:
<key>Location</key><string>file://localhost/volume1/MUSIC/iTunes%20Music/[artist]/[album]/[song]</string>
I got this pattern, especially the use of localhost, from this article. One thing I notice in that article is that he mentions an Import from iTunes option under the Playlists three-dot menu. Even if I create a playlist myself, my three-dot menu doesn’t show this option at all.

Import Process: To create my library, I open the Add Library pane and select Music, then name the library Music. Under Add Folders, I add /volume1/MUSIC. Under Advanced, I enable the Import from iTunes checkbox, and fiddle with a few other settings to make sure my embedded metadata is honored.

Plex scans my library and finds all my music with no problem, and it honors all of my custom genre tags, album art, etc., but my ratings, play counts, and playlists are nowhere to be seen. Hopefully I’ve provided enough information above - does anyone know what I’m doing wrong?

For that matter, what should it look like when I get it right? Should my playcounts etc. come through as everything is being scanned, or should I not expect them to appear until all the music has been scanned and then Plex does a second pass for iTunes data? It’s getting tiring waiting for all 190GB to scan every time before I call it a failure.

EDIT: I guess it’s also worth mentioning that, whenever this process fails, I just delete the library from Plex, fiddle with whatever settings, and try again. Is there maybe something more I should do to have a clean slate between attempts?

…I got it. Turns out the “three dots under Playlists” doesn’t refer to this:

But refers to this:

image

:man_facepalming:

Hope this helps someone else someday.

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