Playlist task "Import from iTunes" does not work

Plex Media Server Metadata & Adding Files
1

Server Version#: 1.18.2.2058
Web Client Version#: 4.8.4

I am using PMS on my Synology DS218+. My entire iTunes folder was meticulously copied with Robocopy from my Windows 10 Pro laptop to the Synology Music share folder. I used the key in opening iTunes and selected the new library location. iTunes came up without issue and all media and playlists are healthy.

I added the the iTunes plugin and properly specified the location of the iTunes library XML path (file name). I rebooted the Synology server as instructed after adding the iTunes plugin. I can see the iTunes Channel in iTunes but it is a mess. It reported 1862 albums after I created my Plex music library (see below). Not sure what functionality this plugin provides.

I added my iTunes library by:

  1. Selecting Music
  2. Specifying the music folder as the iTunes folder under the Synology Music folder.
  3. I selected the checkbox for “Import from iTunes” in Advanced settings
  4. I used the default settings for everything else under Advanced:
  • Genres: Plex Music
  • Album Artwork: Both Plex Music and Local Files
  • Scanner: Plex Music
  • Agent: Plex Music

Plex proceeded to methodically import 925 of the 986 albums from my iTunes library. All the artwork, tags, and ratings eventually got properly populated. I was not concerned about the album miscount as there are known Apple protected downloads that I may deal with through a third party product (e.g., Noteburner).

None of my 27 iTunes playlists were imported.

I created a simple Plex playlist off of my new library as there is no other way to get access to the Playlist task to Import from iTunes. When I tried to use this feature I got the proper dialog box and clicked on Import. I, like many others, received the error dialog “There was a problem importing.” The Import button spins forever and does not complete the task.

I opened the iTunes XML file with Notepad++ and validated that the playlists are at the end of file.

What is the issue with this import feature? I do not want to manually recreate the 27 playlists. It would be nice if I can keep them synchronized with my iTunes library.

2

I am on Windows and feels like I need a PhD in Quantum Physics to do this as well. All songs/albums imports no issue. However, playlists nor any options with … are present to allow me to do anything playlist. Am I losing it or was playlists removed from the advanced “include content from this library…” in the library?