Skip to content
Thoughtful, detailed coverage of everything Apple for 34 years
and the TidBITS Content Network for Apple professionals

How I Dared to Try iTunes Match and Actually Enjoyed It

After the initial public unveiling of iTunes Match (see Adam Engst’s “iTunes 10.5.1 Unveils iTunes Match,” 14 November 2011), I went through the six stages of denial: I was confused about what it was, I was certain it was something I’d never want to try, and so on. My main objection was that it looked to me as if a lot of stuff was going to happen automatically, and I found that scary. Whatever iTunes Match is, it has something to do with my music, and I’ve spent years collecting and tagging that music; I don’t want anything bad to happen to it. I like to be in control. So I decided to ignore iTunes Match.

Then, after a while, I got over it and started doing my homework. In particular, I read a really splendid article over at Macworld. At first, I didn’t understand it. Then I read it again. And again. And after a while I started to get the idea.

What I chiefly understood was this: The main benefit of iTunes Match is, exactly as Adam had said in his article, that it “enables you to store [your music] in the cloud and then play it from any of your computers or iOS devices.” So I could keep, say, 50 GB of music in the cloud, and listen to it on a 16 GB iPhone, even though there isn’t room for it all on the iPhone. In fact, there hardly has to be room for any of it on the iPhone; it’s in the cloud. That is something I did want to be able to do. At the very least, I wanted to try it.

But I wanted to try it gradually. I certainly wasn’t going to approach iTunes Match with my entire music library and say, “Here, iTunes Match, stick this in the cloud.” For one thing, I have 200 GB of music and a rather lame, slow-on-the-uptake DSL connection. For another, there’s a 25,000-track limit, and my library goes way over that. Finally, I didn’t want to hand iTunes Match my real music, because I didn’t want it to come to any accidental harm.

So I started out with a simple goal: get the complete works of Mozart into the cloud, safely, as an experiment. Here are the steps that I followed.

Copy the Music — Everything starts on my computer, with iTunes. What’s going to be important here are the music files. I didn’t want to hand my normal music files to iTunes Match; I wanted to hand it copies.

So, in the Finder, on the Desktop, I created a folder called Mozart. In iTunes, I opened the playlist containing all my Mozart, selected all the tracks, and dragged them from iTunes to the Mozart folder on the Desktop. The result is that all my Mozart tracks were copied to the Mozart folder. Those are the copies I wanted to hand over to iTunes Match.

Make a Separate Library — It’s a little-known but crucial fact that you can have more than one iTunes library — they just can’t both be active at the same time. If you launch iTunes while holding down the Option key, it asks what folder contains your iTunes library, along with an offer to make you a whole new iTunes library folder. So I did that. I had iTunes make a new library in a new folder called iTunes Match, in my Music folder, right next to my normal iTunes library folder, which is called simply iTunes.

At this point I was running iTunes and it had no music at all — because the iTunes Match library was totally new. The new library folder contains all the various files and folders that make up a complete iTunes library, plus it has its own preferences. So, in the Advanced preferences, I turned off the option that says “Copy files to iTunes Media folder.” My goal was to show iTunes some music, and have it put that music in the cloud, but no more; I didn’t want it to keep an additional copy of my music.

Make Some Temporary Music Storage — In the Finder, I created a new folder in my Music folder called Music Temporary. Into Music Temporary, I dragged the Mozart folder that I’d previously created on the Desktop. From there, I dragged the Mozart folder into the sidebar in iTunes.

The result was that the new iTunes library, iTunes Match, now knew about my Mozart tracks and nothing else. And what it knew about was a copy, living in a specific location (the Mozart folder in Music Temporary). That was going to be crucial later on, as you’ll see.

Turn On iTunes Match — Still working in the iTunes Match library, I signed up for iTunes Match. That’s very easy: you click the iTunes Match listing in the sidebar under Store and tell it your Apple ID and password. Instantly it sucks the money ($25) right out of your iTunes account, and voilà: iTunes Match is running.

(I also later discovered that I had received a nice email informing me about the money being sucked out of the account.)

Go To Bed, Twice — The exact details of this step are optional, but you’re going to want to do something time-consuming at this point, because iTunes is now going to analyze your music and start uploading it to the cloud. I reckoned that, given the size of my Mozart collection and the narrowness of my upload bandwidth, this could easily take all night, so I went to bed. In the morning I discovered that I was perfectly right: in fact, iTunes hadn’t even half-finished uploading my Mozart.

Since I needed my Internet connection not to be bogged down with uploading music during the day, I quit iTunes. Then, that night, before going to bed, I launched iTunes again and chose Store > Update iTunes Match. iTunes picked up where it had left off previously, and continued uploading my Mozart for a second night.

Be Amazed on an iOS Device — The next morning I woke up feeling as if it were Christmas. Okay, that’s because it really was Christmas. But I also had found that iTunes was finished uploading my Mozart. I was ready to discover What Hath iTunes Match Wrought.

With trembling fingers I picked up my iPhone and launched the Settings app. Under Music are two switches: iTunes Match and Show All Music. I set them both to ON. iTunes threatened to delete all my existing music on the device, but I just laughed fiendishly, since that was all part of my cunning plan. I had already signed up for iCloud on this device, using the same Apple ID I had used to sign up for iTunes Match on my Mac. So my iPhone should now magically see all that Mozart. Would it?

(I think that right around this moment the iPhone asked me for the password that goes with my Apple ID — I’m sorry I can’t remember exactly when that was. Anyway, I entered it when asked.)

I quit Settings and launched the Music app, and switched to Albums. I could see from the activity indicator in the status bar that the Music app was communicating across the Internet. I waited, and after a while… there it all was! My Mozart tracks are carefully tagged and organized into albums; well, there were all those albums, apparently sitting in my Music app — except that each album had a little cloud icon in its listing. I tapped an album and there were the tracks; and each of them had a little cloud icon as well. Then I tapped a song, and, after a heart-stopping pause, it started to play.



What’s more, it kept on playing. I had started in an album, so the Music app did what it always does when you play a song in an album: it went seamlessly on to the next track in the album.

The really amazing part is that this also works with apps that were written before iTunes Match came along, and that know nothing of its existence. Take, for example, my own Albumen app. Its purpose is to overcome the truncation limitations of Apple’s Music app interface, by showing me the full titles of all my albums, and the full titles and artists of all their tracks — as well as letting me play and pause a track. Well, incredibly, after I’d run the Music app once to update the device’s library, Albumen then showed me all my Mozart albums and tracks, even though none of them were actually present on the device; and if I tapped a track, it started to play.



The only thing Albumen gets wrong is this: Behind the scenes, the way all this cloud-based playing works on an iOS device is that when you start playing a track from an album, iTunes starts downloading that track (so it can play it) and the next track (so it can segue seamlessly into it when it reaches the end of the current
track). Those two tracks, the current and subsequent track, are always missing from Albumen’s display. I presume that eventually Apple will provide new ways for app developers to have their apps survey the Music library so as to take account of this new cloud-based behavior.

Throw Away the Music — My Mozart was now in the cloud. That was where I wanted it. So I no longer needed that special copy of all my Mozart songs that I had made merely for the purpose of handing them to iTunes Match.

So now I did something very bold. I returned to iTunes on my computer, which was still sitting there displaying my special iTunes Match library consisting of all my Mozart. I selected all that Mozart and pressed Option-Delete to remove it from my iTunes Match library! iTunes presented a confirmation dialog containing a checkbox asking me whether I also wanted to remove those tracks from the cloud. But of course that was exactly what I did not want to do, so I didn’t check that checkbox.

My iTunes Match library in iTunes was now empty once again. But those Mozart copies were still sitting in the Mozart folder in Music Temporary, taking up a lot of space. So now I threw caution to the winds and put that Mozart folder into the Trash, and emptied the Trash. (Remember, even they were duplicates of my real music files, which are backed up every which way from Tuesday.)

Meanwhile, back in my special iTunes Match library, I got another surprise, and a very pleasant one at that. The Mozart tracks that I had just deleted were all still listed here under Music — marked with a cloud icon, just like the tracks on the iPhone! And there they remained, reminding me that these tracks, though no longer present on my computer (as far as this iTunes library knows), are stored in the cloud; indeed, if I wanted to, I could actually play them from the cloud, or even, by clicking that cloud icon, download them back to my computer.

Finally, I quit iTunes, started it up with the Option key held down, and told it to open my normal iTunes library once again.

I had done it! Everything on my computer was exactly as it was before. iTunes looked the same as before; and remember, this iTunes library knew nothing of iTunes Match. The amount of space on my hard disk was not reduced; I had made copies of all the Mozart, but then I had deleted those copies. But my Mozart was now in the cloud, and I could play it from any iOS device, or even from some other Mac.

Lather, Rinse, Repeat — Over the next few days I followed the same steps all over again, except that now I didn’t need to make a new iTunes Match-aware library (I already had one) and I didn’t need to sign up for iTunes Match again (I’m good for a year). I quit iTunes and launched it again with Option held down, and opened my special iTunes Match library. I handed it a copy of some other composer’s music. I chose Store > Update iTunes Match. I went to bed.

The result is that all my Beethoven, Mozart, Brahms, and Dvorak are now in the cloud. On future evenings, I’ll probably be uploading the works of a few more of my favorite composers.

Music Management on the Device — Okay, now here’s a problem. Apple’s interface for managing music on an iOS device, when that music is cloud-based music, is not very good. Each time you play a track, it is not only streamed but downloaded and stored on the device. (That’s different from what happens on a Mac, where you can just stream from the cloud to listen.) This is exactly what we were trying not to do: gradually, as you listen to music from the cloud, the iPhone is filling up with actual tracks for which there isn’t enough room.

What you’d like to do, from time to time, is to delete from the iPhone the tracks that are actually present on it. That’s not easy because Apple hasn’t provided a good way of locating them. Here’s my admittedly somewhat awkward solution: Go back to Settings, and under Music, turn off iTunes Match. Now open the Music app again. Under Songs, only tracks that are physically present on the device are displayed. Swipe to delete each of them. The track remains, but it is then marked with a cloud icon, indicating that it isn’t really on the device. Finally, in the Settings app, turn iTunes Match back on.

Dude, Where’s the Matching? — You may have noticed that I’ve said nothing about the “match” in iTunes Match. The idea is that instead of uploading all your music to the cloud, for some of your tracks, at least, Apple may be able to supply a copy of the very same tracks from its own vast music holdings, thus saving you some time and bandwidth.

That aspect of iTunes Match doesn’t interest me very much, however. Some people may be happy that those matched copies are 256 Kbps AAC, which may be better than the quality of the copy on your computer; but my music is already ripped at that bit rate (I can hear the difference when it’s compressed further).

Also, my music is not the kind that Apple generally keeps a copy of. Of about 5500 tracks that I’ve handed over to iTunes Match so far, only about 3500 were matched automatically; the other 2000 had to be uploaded over a series of several nights. I’m not saying that’s insignificant; after all, it’s better than half, which makes the difference between, say, three nights of uploading and six nights of uploading. But in general I wasn’t expecting to be terribly impressed with this aspect of the procedure, and sure enough, I’m not. Your mileage, as they used to say, may vary.

What I am impressed by is, as I’ve already said, the virtual presence of all that music on my iOS devices that in reality are too small to hold it. The seamless display of the cloud-based material exactly as if it were sitting on the device is an utterly successful illusion. I can hardly wait to whip out my iPhone during a discussion of some musical phrase and say, “You know the piece I’m talking about, it goes like this! What? You don’t carry the complete works of Beethoven, Brahms, and Mozart wherever you go?” I’m already practicing a withering look of pity mixed with contempt. Of course, if my interlocutor is a Spotify Premium subscriber, or has iTunes Match as well, that look may have to go unused.

Subscribe today so you don’t miss any TidBITS articles!

Every week you’ll get tech tips, in-depth reviews, and insightful news analysis for discerning Apple users. For over 33 years, we’ve published professional, member-supported tech journalism that makes you smarter.

Registration confirmation will be emailed to you.

This site is protected by reCAPTCHA. The Google Privacy Policy and Terms of Service apply.

Comments About How I Dared to Try iTunes Match and Actually Enjoyed It