iTunes Library on a Mac via Plex Media Server

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I attempted to assist someone on a Windows instance of Plex Server wanting to import their iTunes Library but realized no matter if you had the Plugin activated and had the path assigned to where the iTunes library.xml was, there was no longer import tools or menu items in regards to importing from iTunes, from both Mac and Windows environments. There have been threads in the past about the importing being broken but no one is sure if iTunes importing is going to be fixed.

Adding iTunes library to Plex

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 wi…