One last trick is needed.
6. Create a new playlist by adding one song.
7. Restart PMS. The playlist now appears plus … which permits Import from iTunes.
I still have the problem with 1.18.5.2309 on Mac OSX 10.15.3.
Turning on verbose logging got the playlists from iTunes to load ONCE, but this cannot now be repeated without an error.
The log file shows that all of the iTunes playlists are being scanned and the correct number of tracks have been detected for each one.
These are the last three lines of the log file;
Feb 09, 2020 20:51:17.401 [0x700001410000] INFO - iTunes: done loading 62 playlists and 5 folders in 0.1 seconds.
Feb 09, 2020 20:51:17.401 [0x700001410000] INFO - iTunes: parsed library in 0.8 seconds.
Feb 09, 2020 20:51:17.401 [0x700001410000] ERROR - Exception importing playlists: Invalid library.
The music library is working fine otherwise.
I’m running Plex 1.18.7.2457 on MacOS 10.13.6 (High Sierra) and I have the same problem.
Here’s what I did:
- Deleted all my old Plex data, downloaded a new copy of PMS 1.18.7.2457 and ran it
- Enabled the iTunes plugin, did not set a library XML path.
- Created a Music library, ticked the import from iTunes option
- Library imported fine, but no playlists, ratings etc. I don’t really know what that checkbox is meant to do…
- Created an empty playlist so the “Playlist” menu item option would show up
- Clicked the three dots on the Playlist menu item and clicked “Import from iTunes”
- An error message flashes up. In the log I see:
Feb 29, 2020 09:39:19.638 [0x70000156f000] Info — AutoUpdate: no updates available
Feb 29, 2020 09:39:28.917 [0x7000017fe000] Info — iTunes: loading playlists...
Feb 29, 2020 09:39:28.958 [0x7000017fe000] Info — iTunes: done loading 1 playlists and 0 folders in 0.0 seconds.
Feb 29, 2020 09:39:28.958 [0x7000017fe000] Info — iTunes: parsed library in 0.6 seconds.
Feb 29, 2020 09:39:28.959 [0x7000017fe000] Error — Exception importing playlists: Invalid library.
Feb 29, 2020 09:39:28.959 [0x7000017fe000] Warning — Could not find path: /Users/henry/Music/iTunes/iTunes Media/Music/Edguy/Theater Of Salvation/06 Falling Down.m4a
... [more errors for every file in my library]
I did another test on my Windows 10 PC. Installed a fresh new version of Plex, imported the music to a new Music library, then tried importing playlists. I only had one playlist set up in iTunes. The import failed as normal.
I realised most of the songs in the playlist werent actually downloaded and were in iCloud Match instead. I downloaded all the songs and re-tried it and it worked! Even brought in the ratings, which is what I actually wanted. Going to do some more testing with a larger library and more playlists and see how it goes.
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Hi guys !
Looks like I have smg equivalent to your problem …
Any suggestion ? 
#EDIT :
Thanks @Bunkermentality it worked !! 
Your iTunes xml file will have a path to every music file in iTunes. That path needs to look the same to plex server. If you plex server cannot read and process that path to the actual file, it wont work. Might that be the issue?
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Hi Allan ;
I am there now 
iTunes playlist import was broken for me too, with the Plex server returning a 500 Internal Server Error.
However, based on henrysingleton’s post, I checked, and there were a number of songs that I’d purchased from iTunes on a different computer that hadn’t downloaded / were still in the cloud, and after clicking to download them all, running the iTunes playlist import worked! Yay.
Would be great if Plex’s server errors gave more useful error details/messages.
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