Moving from iTunes to Plex Music

Usually, I just search for a blog post that would already have this information, but I couldn’t find one. So I decided to write up this experiment.

I don’t like the iPhone Music app. I find the experience of browing, organizing, and listening to music with it is poor, and rating music with it is both not fun and not reliable. Something that used to just work” simply doesn’t now. But there’s a bigger problem than the iPhone app.


iTunes doesn’t save ratings (either stars or hearts) reliably. Sometimes you’ll rate a song on your phone and that rating simply won’t appear anywhere else. Or it will, but then it’ll disappear next week. There’s data rot going on here, and it’s hard to predict, find, and eliminate.

On top of that, iTunes will try to help” your ratings by rating your albums using an average of already-rated songs. So if you’ve rated one song in an album 2-stars, the whole album will get a 2-star rating. This essentially destroys smart playlists, and has infuriated many.

But the main problem is that iTunes is a relic now, and star ratings are so far down the scale of importance at apple that they’ve been reduced to a feature that isn’t even on by default. Apple has shifted its resources to its subscription service, Apple Music, and iTunes remains alive, but is clearly on the back burner.

Last thing: iTunes doesn’t work great with two computers, and works even worse when those two computers are on at the same time.


Plex does a lot of similar things to iTunes. But it’s better at working with multiple devices (I can now listen to my music on my TVs again), and so far as I can tell, a rating will stay the way you want it to until you change it. That’s not something Apple Music or Spotify can promise. That sort of stability is getting rare.

Plex is also just a nicer experience. It has a lot of Zune-style features like artist info and related links. It feels like an app pushing you to explore and enjoy your collection.

The integration between Plex and iTunes is a single option inside Plex, called Import itunes playlists. Somewhere in settings, you can toggle song ratings as an option for import. The secret feature here is that song ratings also come through. So all that work you put into rating songs in iTunes moves over to your new library.

This is a one-way exchange of information, from iTunes to Plex. It doesn’t work the other way. You can do it as often as you like, however. So if you’re just simply interested in keeping your metadata in iTunes going forward, and just want your playlists in Plex for convenience, this is an easy way to keep the two in sync so long as iTunes remains the home” for your playlists and ratings.

Other Findings

  • Removing a rating from iTunes does not remove it in Plex, even after a fresh update.
  • Changing an existing rating in iTunes does update it in Plex. The new iTunes rating will overwrite the old Plex rating.
  • Plex can always import more ratings. So you can still use the iPod to rate music, and then just hit the … and hit import itunes playlists”
  • This does not work the other way. Rating a song in Plex will not result in the rating being shown in iTunes.
  • Much like this redditor, I haven’t been able to find a way to take a Plex playlist and get it into iTunes.
  • Song that have been Album rated” in iTunes show up with that rating in Plex. So if iTunes decided that a whole album was three stars because you rated one song three stars, the whole album shows up in Plex with three stars.
  • In running this experiment, I’ve come to realize something about album ratings: I think iCloud is messing this up, and that if your rating column has a grey number in it, it may have actually been your rating. Because while I have grey rated songs, I also have songs that have album ratings but no song ratings.
  • My personal use case would involve syncing a playlist offline in Plex, and then rating songs on the go. This does work, but the info doesn’t always sync back quickly. But once it does, it stays there.

So why keep iTunes around?

iTunes Match, basically. It’s still a phenomenal service. It’s like an amnesty program for mp3s. iTunes doesn’t care where they came from. Add a file to your iCloud library, and they’ll replace it with their own higher quality one, and it’s still a file you can use with any device (these files load just fine on a Zune).

This is where iTunes Match still comes in handy: Deleting a file in plex deletes the local file from your computer, but if that song is uploaded or matched in iTunes Match, the file simply becomes stored in the cloud. So you can keep a clean” library in Plex, while keeping everything in iTunes Match.

Season of 1.1

I know this seems like a big jump, but it really isn’t. I’m still using iTunes, but it’s more of a backend archive/file organizer now, and Plex is the place where I can actually enjoy the process of listening to and organizing my music. It’s nice so far.

Plex Music

May 11, 2018