Why can I re-import playlists in MacOS, but not Windows?

Why can I re-import playlists in MacOS, but not Windows? I’ve done these dozens of times in MacOS Plex Server from updated XML files fast without any issues.

In Windows, I have to use Soundiiz and import one playlist at a time after generating them one playlist at a time from Music. And then it is unreliable.

Forgot to show an example of what you see in the dropdown options for Playlists in MacOS and Windows.

You can only import from iTunes and it needs to be installed on the same computer the server is installed and the server needs the iTunes plugin enabled with the path to the iTunes xml file

I have iTunes installed on my Dell XPS Windows 10 laptop and the IDs use to login into both Plex and iTunes are the same as the IDs I use on my macOS Catalina. Both operating systems have the latest version installed on them.

I first noticed this several months ago when I first installed Plex server on my Windows box. While I had a correct path entered to the iTunes XML file, Plex did not import my playlists when I first created my library in Plex. Plex found all my albums, songs and artwork just fine when I created the library, but did not import my playlists when the Library was created. I deleted Plex and reinstalled several times and again created the music library several times. Also I tried just deleting the Library and reinstalled it in Plex without reinstalling Plex server.

I looked for the iTunes plugins on my Windows box every time I reinstalled Plex server, under “Manage” > “Plugins” and have never found the 2 plugins I have on my Mac - ITunes Music and iTunes Videos. I have searched Plex and the Internet to find out why and how to get these iTunes plugins installed on my Plex server on my Dell box to no avail.

Since these plugins are not in my Windows Plex server, I understand way I can’t installed my playlists from the iTunes generated library XML. So, I need them installed somehow.

It is not in the “Manage” area. On the left under the Library settings.

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