TL;DR version: ALL menu options to IMPORT iTunes Playlists have been removed from all Plex Web iterations, but the Plugin settings still remain, though there is no clear indication that IMPORT iTunes Playlist functionality will ever comeback. I have solely been on a Mac environment for the entire time of running my Music Library and it’s been a while (I’m talking like 2019) since I had to last import or had a use for iTunes altogether. I’ve documented my steps with a fresh install and was met with no success of even seeing where the importing is involved like it use to. I’d say find another way at this point. Plex has stopped allowing iTunes Playlist importing and should REMOVE plugin settings accordingly since functionality is useless.
This option no longer exists and neither do the menu options (see below)
There are no signs of being able to import playlists via:
- Plex.tv Web App
- Plex for Windows - localhost: http://127.0.0.1:32400/web/index.html
- Plex for Mac - localhost: http://127.0.0.1:32400/web/index.html
Windows 11 Environment
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iTunes Version: Version 12.12.2.2 - Installed via Microsoft Store
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Plex Media Server for Windows, Plex Pass Download Build: 1.25.6.5545-c8bd13540
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Fresh install on a laptop that never had iTunes nor Plex Server installed.
I opened up iTunes, fresh install, went into Preferences and CHECKED Share iTunes Library XML with other applications (highlighted in GREEN).

Imported some music albums, made some playlists (seen below) and closed iTunes entirely.

Installed Plex Server, added a Music Library, imported iTunes music library using following path: C:\Users\username\Music\iTunes\iTunes Media\Music
Go to PLUGINS in the Plex Server and CHECK Enable iTunes Plugin.
Next open up File Explorer, go to Music, iTunes, and right click on the iTunes Music Library.XML file, then COPY AS PATH.

Paste this copied path into the iTunes library XML path field on the Plugins page.

SAVE changes.
EXIT Plex Server using the Taskbar icon. Shut it down.
Reopen Plex Server.
End Result: Plex has stopped allowing iTunes Playlist importing and should REMOVE plugin settings accordingly since functionality is useless.

