Itunes Playlist Import Revisited

Plex Media Server
1

Server Version#: 1.20.1.3213
Player Version#: 4.34.4
I had to modify my music files due to Plex not handling multi-album sets correctly. This resulted in many changes to folder names. This resulted in all of my previously imported playlists from Itunes getting broken as it now cannot find the files. So, I tried to import again. Fails. Near the top of the Server Log for the import, it says
Sep 19, 2020 08:35:59.688 [14440] INFO - iTunes: done loading 55 playlists and 0 folders in 0.0 seconds.
Sep 19, 2020 08:35:59.688 [14440] INFO - iTunes: parsed library in 0.4 seconds.
Sep 19, 2020 08:35:59.688 [14440] ERROR - Exception importing playlists: Invalid library.
Sep 19, 2020 08:35:59.689 [14440] WARN - Could not find path: “E:\Jukebox2\2002\Land of Forever\01 Summer Of 300 Years.mp3”

then there are errors like the last one for EVERY file. Now, looking at some old posts, it appears it’s cranky about exact matches in file names, but it appears to me that mine do match. Is this just not going to work? I don’t know what “Invalid Library” means. Is that my Plex library or the Itunes XML file? I tried changing the XML file to put the individual file names is double quotes, but it does not work. Any help or ideas appreciated.

How do you import an iTunes Playlist?
2

OK, so, being stubborn, I tried exporting a single playlist to an XML file, then changing the Plex “plugin” to point to that file, then doing an import playlist from Itunes. This worked, much to my amazement. Now, doing them all this way is a bit of a nuisance, but it seems to make it possible. At this point, I’ve only done one, so it can still bite me.

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Nope. Only worked once. Now doing the same as in my original post, even with the same XML file. Giving up. Obviously some kind of Plex bug.

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