Heyo, I’m trying to migrate my iTunes ratings, playcounts and playlists into Plex. I guess I’m not the only one trying to achieve this, since there is even a landingpage dedicated to this. Yet there is a lack of documentation regarding this process. I’m happy to contribute documentation in form of a post. You just gotta pinpoint me to whats missing tho, since I’ve got neither ratings, playcounts or playlists showing up in plex yet 
My approach so far:
OS: Windows 10
PMS: 1.20.3.3437
Plex Web: 4.34.4
iTunes plugin:
- Activate iTunes Plugin
- “Show Advanced” and provide path to iTunes library XML path:
C:\Users\Sebastian\Music\iTunes\iTunes Music Library.xml
Adding a new library:
3a. Add iTunes folder “C:\Users\Sebastian\Music\iTunes”
Alternatively:
3b. Add the Music folder which has been mangaged by iTunes “C:\Users\Sebastian\Music\iTunes\iTunes Media\Music”
Setting Advanced Options:
The music is there but neither 3a, nor 3b imported ratings, playcounts and playlists into Plex. What am I missing?
