How to sync iTunes playlists to Plex on a Mac

[jlightfoot]

Server Version#: 1.18.3.2156

I figured out how to synchronize Plex with iTunes playlists on a Mac. I have an old Macbook Pro running High Sierra that hosts my Plex Server. This is only known to work with iTunes, not the new Apple Music app, so it probably won’t work if you are running macOS Catalina.

1. In iTunes, select Preferences/General, then make sure “iCloud Music library (yourappleid@apple.com)” is checked. This allows you to share playlists from your other devices via your iCloud account with your Plex server.

2. In iTunes/Preferences/Advanced, check “Share iTunes Library XML with other applications.” This creates an XML file with data about your music library that Plex uses to integrate.

3. On your Plex server, select Settings/Plugins. Check “Enable iTunes Plugin.” In the iTunes library XML path field, enter “/Users/your_Mac_id/Music/iTunes/iTunes Music Library.xml”. Check that this file exists. It should if you did step 2. Click Save Changes.

4. Restart your Plex Server. Right-click on the Plex > sign in the menu bar, select Quit, then restart Plex Server from your applications menu or launchpad.

5. If all this has worked, you should be able to go to Manage/Plugins in the left-side menu in the Plex client and see the iTunes plugin.

6. I had a hard time figuring out where to see the playlists. What I did was to open one of my albums in the Plex app, select a song, then on the 3-dot menu chose “Add to playlist…” to create a Plex playlist. I then used the Plex search at the top of the app to find the playlist I just created. Once I picked it, it magically created a new choice, Playlists, under the main Plex app menu where Home/Web Shows/News/Podcasts /Music/etc. were. There’s probably a better way to do this, but it worked for me.

7. On the 3-dot menu on Playlists, choose ”Import from iTunes…” All of your iTunes playlists should download to Plex. I have Apple Music, so some of my playlists contain songs from my library and songs from Apple Music – Plex can only download the songs you own in your own library.

Enjoy,
John