It’s been almost exactly 4 years since iTunes Match was introduced, and the service still has issues syncing metadata. I discuss this problem in this week’s column, and I also explain how to customize the graphics that display in iTunes’ Playlist view. And I present The Essential iTunes Keyboard Shortcut™, which every iTunes user should know.
iTunes Match not updating
Q: I’ve subscribed to iTunes Match for the last few years and I’ve been impressed with the service. However, there are problems with play counts updating (or not). Sometimes I’ll listen to a bunch of music on one device and play counts will sync instantly. Other times I can listen for hours and only the first song’s play count will sync, and it can take several days before the rest are updated. This means that many smart playlists I have, which are based on play counts and last played dates, are different across my devices.
Is there something I’m missing or is this just a fault with iTunes Match?
The promise of iTunes Match—which is now part of iCloud Music Library—is that your music library syncs across your devices. Apple says that “When you create, edit or delete a playlist on your Mac, PC, iPhone or iPad, those changes will sync across any iTunes Match–enabled device you own.” This suggests that smart playlists, based on criteria such as play counts and last played dates, also update, because this metadata updates these playlists.
As the reader points out, this updating is inconsistent and has been since the launch of iTunes Match four years ago. Apple has given mixed messages over the years, with some iTunes Match users hearing from Apple support representatives that iTunes Match isn’t designed to update this kind of metadata, and others saying that it should update within 24 hours.
I’ve had both types of experiences. In some cases, iTunes Match updates this metadata relatively quickly, and in others, it takes days or never updates. I have several smart playlists that are based on play counts or last played dates, and I’ve given up expecting them to work. I recommend that you don’t lose sleep over it, and accept that iTunes Match just doesn’t work as expected.
Playlist graphics
Q: When I make a new playlist in iTunes, there’s a header above the song list, and that header includes artwork from the music in the playlist. It seems to take four albums at random and makes a sort of mosaic of their covers. Is there any way I can change the artwork in the playlist header?
New in iTunes 12 is the playlist header. As you can see below, for this playlist of selected Brian Eno albums, iTunes has chosen four covers to make the playlist graphic.

iTunes chooses which album covers it uses to make playlist graphics.
You can’t alter which albums iTunes chooses for the playlist graphic after the fact, but if you add albums to a playlist one at a time, iTunes uses the first four albums (or songs, if each song has different artwork) to create this graphic. So if you want to use four specific album covers for a playlist graphic, add those four albums (or songs) first, then add other items.
Another way you can change this graphic is by dragging any image to the playlist header, and dropping it on the graphic. iTunes then replaces its auto-generated image with the graphic you dragged. So you could have a single cover for a playlist with dozens of songs, and dozens of different album covers, or even use a photo of an artist, of a live performance, or your pet.

My cat is a big fan of the Grateful Dead, or at least he hasn’t told me yet that he doesn’t like the band…
It seems, however, that the only way to delete any custom graphics you add to the playlist header is to replace it by dragging something else on it. You could also make a new playlist, copy all the music to it, and let iTunes generate its own graphic. You can then delete the original playlist.
iTunes losing its way
Q: Sometimes I listen to an album in iTunes and see its track list in the iTunes window. I then switch to a different app, and, when I return to iTunes the album list has moved and I have to search for the album I was listening to if I want to, for example, change tags for any of the album’s tracks.
Is there any way to prevent this from happening? To just make iTunes stay where it was when I switch to a different app?
I don’t see the same thing as you, but sometimes iTunes does switch to a different view. I don’t know of any way to prevent this, but I am well armed with The Essential iTunes Keyboard Shortcut™.
No matter where you are in iTunes, no matter what type of content you’re playing, if you press Command-L, iTunes switches to show the currently playing item. If you’ve started listening to music, for example, from your Music library, iTunes will show you the currently playing track in the overall Music library. If you’re listening to a playlist, iTunes beams you back to that playlist.
Learn to use the power of Command-L, and iTunes will be just a tiny bit better.
Have questions of your own for the iTunes Guy? Send them along for his consideration.