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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.


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Comments about How I Dared to Try iTunes Match and Actually Enjoyed It
(Comments are closed.)

Joseph Goldberger  2012-01-04 17:18
The music I want to use from ICloud are Broadway show albums. I am having a problem on ITunes because for some albums it skips tracks. I do not want ICloud to “match” songs from my albums. I like the original. What say you?
Matt Neuburg  An apple icon for a TidBITS Staffer 2012-01-04 17:34
I've no objection to the "match"; it's not a substitution of a different performance, but the very same track. How Apple does that is, I believe, a closely guarded secret. But it does work; it didn't misidentify any of my tracks.

As for the skipping of tracks (I assume you mean they aren't being uploaded), I find that, unless there is something wrong with the track itself, waiting a day and choosing Store > Update iTunes Match gets the uploading going again.
Simon Robins  2012-01-04 17:33
I think that the fact that songs are downloaded onto an iOS device but can be streamed to a Mac and Apple TV is a conscious decision by Apple to keep the usage of your monthly mobile data allowance to a minimum. I like the way iTunes Match works in this respect.
I am having a bit of a problem with my iTunes Match because I have the Beatles Mono box set, which iTunes insists on matching with its stereo copies of the same songs. Haven't figured out a way around that one so far.
Kendall  2012-01-04 21:56
This kind of thing is my concern. As it is, iTunes suggests incorrect artwork -- sometimes wildly incorrect -- when I use Get Album Artwork, seemingly matching on any random word sometimes (not even using the right artist!). Other times, with albums I believe it should find, it says it can't find me artwork.

I know the music matching is deeper than this -- well, from what I've read, it sounds like it -- yet with various versions (sometimes from the same album) of a song, I'm worried I'll get the wrong stuff.
Matt Neuburg  An apple icon for a TidBITS Staffer 2012-01-05 06:19
Both of you are raising profound issues. Basically iTunes Match is too early and too simple. Apple had released it into the open without considering interface or options; they didn't consider people's real needs and desires deeply enough. A simple checkbox ("Upload, don't match") would have done the trick here. Maybe Apple will eventually do that.
Matt, you really didn't keep a backup of all that music? Very dangerous indeed. Because you may find, when you finally get to listen to all that music, that some of the tracks are messed up, like this:
Nicholas Barnard  2012-01-05 02:05
Kirk, he did keep a backup, just not in the iTunes Match iTunes library. (Remember that he has TWO iTunes Libraries..)
Matt Neuburg  An apple icon for a TidBITS Staffer 2012-01-05 06:15
Yup, what I handed iTunes Match was already a copy - a copy of the tracks in my *real* iTunes library, which I do keep backed up (twice).

In fact, it was a copy of a copy! I also keep all my original, uncompressed tracks - and I keep *them* backed up too (twice).
Jon Doty  2012-01-05 11:55
After reading this article and the comments I'm afraid there is still lingering confusion about what iTunes match does with your local music library. When iTunes match performs the matching/upload process, it does NOT modify the files on your HDD. It doesn't even update their ID3 tags. The only way your music library could change is if you manually downloaded tracks from the cloud. So I don't understand the purpose of using a secondary iTunes library to upload tracks.
Matt Neuburg  An apple icon for a TidBITS Staffer 2012-01-05 16:12
First, iTunes Match wouldn't have accepted my real iTunes library, because it exceeds the track limit, as I said in the article.

Second, I didn't want to put all of my music in the cloud, just selected tracks - and I didn't know of any way that iTunes Match would allow me to do that (and I still don't).

Third, I didn't want to occupy immense amounts of time uploading, so I used a second iTunes library and gave it the particular music to upload in small stages during successive night.

Fourth, you can *say* it won't modify the files, but I wasn't about to take any chances.
Jon Doty  2012-01-08 19:47
Thanks for the clarification, Matt, and thanks for the article.
Kendall  2012-01-05 19:33
I commented but was not confused. I've read lots before now, mostly at Matt's article was quite helpful and opened me up a little to iTunes Match, although I don't need it. But I've read a few comments elsewhere about mismatched songs, and my two comments about that are:

1. If I'm on the road listening and discover a Matched song is wrong, that's frustrating. Not a big deal, but how do I resolve it?

2. If as some people recommend I use Match to "upgrade" lower-bit-rate songs (e.g., pre-iTunes Plus), and get the wrong song, that's beyond frustrating, and trying to double-check 500+ lower quality purchase is kind of a nightmare. I realize MATT wasn't suggesting using iTunes Match to upgrade (delete songs; redownload from Match), but Macworld's pushed this a lot and clearly there's danger there. Backups are great but listening to 1000 songs (500 songs, twice)...yucko. ;-)

I love Matt's idea of a secondary library for that reason. I could make a long-term project of upgrading tracks using iTunes Match (and have the primary purpose of it while I'm at it, of course, but I don't need that).
Walt French  2012-01-07 08:32
“If I'm on the road listening and discover a Matched song is wrong, that's frustrating. Not a big deal, but how do I resolve it?”

Good question, but how likely is this? I'm not talking about mono vs stereo, but the kwazy mismatches I sometimes see in SoundHound or Shazzam.

It'd be nice to see some decent statistics on how accurate the match function is. Especially for those of us with large libraries (I think of my 8800 tracks as pretty large), a late discovery of a mismatch might be after we'd erased the original and it becomes a big, bad deal.
I think the matching process has changed some since the initial rush of iTunes Match because it seems to do a much better job of getting all the tracks in an album and of not making crazy stupid matches, but in that first week or two I did have a lot of mismatched tracks. I'd go to play something like Coldplay and I'd get some late 1950s blues instead. My library is large, so I ended up removing everything from iCloud and redoing it (which took several days) because I wasn't willing to go through 24,000 tracks manually.

As for iTunes not changing your local files, that is true, but since my primary use of iTunes is to listen to music on my iPhone, getting the wrong tracks matched in the cloud is an issue because those are the tracks I hear. So yeah, my local Beatles Mono are still in Mono, but when I hear them on my iphone I'm hearing the stereo version instead.
AHoffman   An apple icon for a TidBITS Supporter 2012-01-05 18:54
I have a problem that Apple has yet to figure out.

I have tracks that Apple DOES have but does NOT match. I mean, iTunes Match recognizes most of the album, but not all of the tracks on the album.

For example, The Beatles' album, Please Please Me. It does not recognize and match tracks 3, 7 (title track), 9, 11 & 14.

Total unmatched tracks? About 15%. Maybe 2/3 of those should have been matched.

I reported this, and we've gone back and forth a few times. No reported solution.
Conrad Hirano  2012-01-05 20:53
A friend ran into the same problem with a few Beatles tracks, so I replaced her files with copies of the unmatched tracks from my library. iTunes Match was subsequently able to match all of those tracks.

My tracks were ripped from the Beatles stereo box set, so they should match the corresponding tracks available on the iTunes Store. Hers were probably ripped from the original CDs. Perhaps the differences were enough to cause the matching algorithm to fail for those particular tracks.
Seth Elgart  2012-01-10 04:39
When I'm at home I don't need to stream because I've got all my music right there, but the point of iPhones and iPads is that they're portable. So, what happens when you're in the subway? Or what about on a bus between New York and Boston, say, that goes through several spots that have well, spotty cell coverage? Or on a plane? It just seems to me that the places you'd need it most won't necessarily have streaming available.

My other question is about bandwidth. An hour's worth of music might be 100 MB, so my four or five hour trip to Boston might be almost half a GB. I only have 250 MB of 3G data on my iPad data plan per month. In a world with unlimited free bandwidth iTunes Match makes perfect sense. We just don't really live in a place like that.

It just feels like I'm missing something here. It's great for matching music on computers that don't move, but it just doesn't make all that much sense to me for streaming to portable devices that rely on data-limited connections.
I use iCloud to grab an album or three at a time when I am on wifi (which is, honestly, mot of the time). Yes, I sometimes stream, but I am more likely to do something like grab a playlist while at the coffee shop or even stopping by a local McDonald's. Downloading a few hours of audio only takes a couple of minutes.

What I have noticed is that the 'Artists' sort on the iphone is completely useless. Listed under 'P' I have Tangerine Dream, Keny ROgers, Leann Rimes, Julie Cruise, Bettye Lavette, Klymaxx, Julie Andrews, Disney, Mary Martin, and many other non-Q names. I have to type a specific artist name into the search field to find, for example, Queen. Then I get 8 artists as results, 4 of which are "Queen" and the other 4 are "Queen / George Michael", "Queen / David Bowie", "Queensrÿche", and "Queen / David Bowie" (again).

It's a big mess, especially since other than Queensrÿche, all those 7 "results" seem to lead to the exact same list of albums and tracks.

And don't get me started on iTunes and audiobooks. If it didn't make me so mad, I could write a whole article on just how terrible iTunes is for Audiobooks.
John Baxter  An apple icon for a Friend of TidBITS 2012-01-10 19:58
Matt, I believe based on reading that although the Music app is downloading and keeping tracks from the cloud, it doesn't keep them obsessively. When it thinks it has too many bytes of music, it will start deleting based on some modified least recently used algorithm.

I'm not able to test this idea (too much memory on my iDevices--too little music). But you should be able to pretty easily given your collection.

And thanks for the article! It's one more place I can point people who ask about iTunes Match.

I may be close to an adventure: loading iTunes on my Windows machine (Windows folk complain about how bad iTunes is--it's hard to convince them that it's nearly as bad on the Mac), and then introducing that iTunes instance to the purchased music Zune known about on my machine and running that through iTunes Match.


Mark Hennon  2012-01-10 22:14
Matt, that article is a delight. Congratulations, and Thank You!