iTunes Match Still Kinda Sucks

Just saying…


That’s the mono version of Miles Davis’ Milestones. Which is on the iTunes Store.

I added all nine CDs from the Miles Davis: The Original Mono Recordings to my iTunes Match library, and, out of 70 tracks, 51 matched and 19 were uploaded. That’s a match rate of 73%.

Sure, I’ve got some discs where all tracks match, and others where none match. But Apple really needs to improve the matching algorithm; it’s simply a failure that only 3/4 of the tracks on these 9 albums, which are in the iTunes Store, match. (I ripped them in iTunes Plus format, 256 kbps AAC, but the format should have no effect on the accuracy of matches.)

001.pngRead what Apple says about matching: “And for the few songs that aren’t…” In other words, they suggest that only a handful of songs won’t match because they’re not available from the iTunes Store. But I’m not writing here about songs that aren’t in that pool of 26 million; I’m writing about the ones on albums that are in the iTunes Store, where only some songs don’t match.

I can point to any number of albums where one track doesn’t match. For example, the last track on each of two Grateful Dead albums, American Beauty and Workingman’s Dead, gets uploaded. And these are two of the Dead’s most popular songs: Truckin’ and Casey Jones. If you use iTunes Match, I’m sure you see the same thing when you scroll through your library.

So, yes, iTunes Match still kinda sucks. Apple needs to improve the matching algorithm. Oh, and raise the 25,000 track limit too.

Note: I spotted something interesting when looking at this set in the iTunes Store. I have 70 tracks, and the iTunes Store says “79 items” for the set. I checked each album, and they’re the same. So the iTunes Store counts the album itself as an “item.” I think what’s happening is that the iTunes Store listing has one line for each album name, as well as one line for each track; hence it is counting each line as an item.

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16 replies
  1. Scott Atkinson says:

    Ok – I thought it was just me. I got an Amazon gift card for Christmas and decided to buy the Herbie Hancock “Acoustic Collection” (roughly half of the spendy “complete Columbia” set) as mp3s. Instead of matching, iTunes basically uploaded the entire collection. I haven’t been able to figure out how to delete the mp3s and substitute the 256k aac files, something I’ve done many times in the past with both mp3s and burned cds.

  2. Michael Lach says:

    Very helpful. Sure wish the 25k track limit would be raised soon–can’t effectively even try iTunes match unless that gets changed. I’d be happy to pay more to sync a large library…

  3. Doug Adams says:

    Get out of my yard, iTunes Match! I’ve gone old skool: back to manually managing music on my devices, and relying more on Home Sharing and AirPlay.

    • Kirk McElhearn says:

      I don’t really use it. I have a test library so I can write about it, and I have it set up on my iPod touch, which I use for listening sometimes. It’s practical if you have fewer than 25K tracks, and want to change what’s on your mobile device, which doesn’t have enough space for everything, without syncing. Also, my son loves it, because he can listen to anything from his iTunes library on the Mac he uses at work. This said, he’s just hit the 25K limit…

  4. andrewmagruder says:

    I agree with the basic point that iTunes Match needs to match more often. I *really* want to know why it doesn’t. That said, YMMV, but 25,000 exceeds the capacity of every iOS device I own by a huge margin. So having an even larger potential library really wouldn’t help me much.

    Instead, I’d greatly prefer the option to use Apple’s metadata for any file which does match. Even if I have to go through the bother of selecting from a small possible list of metadata sets to use on a per file basis (i.e. original release vs. greatest hits album release.) The 3rd party tools to do this are as wobbly as iTunes Match is at matching…

    • Kirk McElhearn says:

      Isn’t part of the point of iTunes Match so you _can_ have more music in your iTunes library than on your device, and download what you want when you want?

  5. Wayne B. Hewitt says:

    I, too, can confirm the lack of matching. Not counting books from CDs, I have about 220,000 tracks from over 18,000 named albums. Of all these about one sixth have never matched. To get this many matches I use a “sandbox” strategy where the active iTunes match User never has more than a few thousand tracks, i.e., my working iTunes library is not the same as my music archive.

    Even though I used some tricks to successfully match some hard to match tracks, many were simply “unmatchable.” This seems to be irrespective of how or when the tracks were ripped or acquired.

    • Kirk McElhearn says:

      Are these tracks that are available from the iTunes Store? I don’t expect everything to match – there are small, obscure labels, and old recordings – but I expect tracks in the iTunes Store to match.

      • Wayne B. Hewitt says:

        I can understand the non-matching of old or obscure albums, but to have so many albums that match except one or two or three tracks defies explanation. Now there are some albums where the last couple of bonus tracks do not match, but those are the exceeption.

        Let’s look at what’s new this week on the Billboard ‘Top 200:’

        Above & Beyond (2014) – Acoustic - All Matched
        Blessett, Algebra (2014) – Recovery - All Uploaded
        Casting Crowns (2013) – Thrive - All Matched
        Crosby, David (2014) – Croz - All Matched but Track 3
        Dum Dum Girls (2014) – Too True - All Matched
        The Gaslight Anthem (2014) – The B-Sides - All Uploaded
        Grace, Jamie (2014) – Ready To Fly - All Matched
        The Lawrence Arms (2014) – Metropole - All Matched
        Mineo, Andy (2014) – Never Land - All Uploaded, Listed as “Purchased”
        Of Mice & Men (2014) – Restoring Force - All Uploaded
        Periphery (2014) – Clear - All Uploaded
        Rashad, Isaiah (2014) – Cilvia [Demo] - All matched but Tracks 10 &14
        Red Dragon Cartel (2014) – Red Dragon Cartel – All Matched
        Smith & Myers (2014) – (Acoustic Sessions) -All Matched
        You Me At Six (2014) – Cavalier Youth – All Matched


        Aer (2014) – Aer - All Matched but Tracks 8, 12
        Hard Working Americans (2014) – Hard Working Americans – One Track Matched of Eleven
        Mogwai (2014) – Rave Tapes - All Matched but Track 10 (Last)
        Scorpions (2013) – MTV Unplugged - All Matched but Track 13 (Last, CD 2)
        Stone, Joss (2004) – Mind, Body & Soul - All Matched but 15 (Hidden)
        Stone, Joss (2009) – Colour Me Free - All Matched but Tracks 4, 5, 12
        Stone, Joss (2011) – LP1 - All Matched but Track 5
        Ty Dolla Sign (2014) – Beach House - 2, 5, 6 Matched; 1, 3, 4, 7 Uploaded

        This has been an ongoing pattern since iTunes Match began.

  6. Brian says:

    Here’s an idea, don’t buy it next year. I think it’s an incredible steal for $25 a year. None of the other ‘services’ has anything remotely comparable (IMHO) let alone also tossing in ADD FREE iTunes Radio to boot (a point you completely omitted).

  7. Scott Atkinson says:

    Kirk -

    You got any idea why something like what I describe above would happen? iTunes and the Amazon mp3 store both offered the Hancock acoustic set in identical versions, but Match didn’t recognize the mp3 files at all, so I’m stuck in a loop where Match uploads the mp3s, and if delete them to try to get aac files instead, iTunes no longer “knows” I own the album. I see no way to substitute the iTunes files for the Amazon files. One thought: the iTunes version is marked “mastered for iTunes.” Could Apple be forcing me to use the mp3 files because it views the “mastered for iTunes” as an upgrade, which I’m not entitled to? If so, that’s strange, because when I’ve ripped cds and encoded as lossless files, iTunes has had no issue provided “mastered for iTunes” substitutes. Maybe I don’t understand Match properly…

    • Kirk McElhearn says:

      If the only version is Mastered for iTunes, that’s what you’ll get. It seems like you have a very odd case here. Unless the files are radically different – such that iTunes can’t match them with its digital fingerprinting – I don’t see why this is happening. Can you send me a file? Send me an email via my Contact page and I’ll reply; if you can send me the shortest file, I’ll try and match it and see what happens here.

  8. Simon P. says:


    Another rather annoying issue with iTunes Match is having tracks that were purchased from iTunes and matched never playing from iTunes in the cloud because the songs are no longer available, yet iTunes still matches them. Apple Support couldn’t figure it out and suggested I burn then rip them, which I’ve yet to do, mainly because I’m stubborn and think it’s stupid and I shouldn’t have to do that.

    Selecting Show in iTunes Store for the E.P. or tracks takes me to the artist but different tracks. The store still has versions of the tracks but not longer the remixes, which is what I purchased.

    It’s only two tracks but quite tedious, since I listen to my music at work via iTunes in the cloud.

  9. Mike Burgess (@mikentosh) says:


    I was wondering if you have seen an issue where just one song is unplayable.

    My Pink Floyd: Wish You Were Here album was ripped from my CD and I have uploaded it using iTunes Match. I couldn’t get the first track, Shine On You Crazy Diamond, to play from my iPhone or iPad afterwards. It would simply just skip to the next track every time it came up in rotation. I went to the Genius Bar, I volleyed support emails with Apple and nothing they suggested would work. They placated me with three free tracks which I thought was nice. I finally just directly synced my iPhone to my MBPR and it plays. Since that first trip to the Genius Bar almost a year ago, I have purchased a new phone and of course upgraded the OS used iTunes Match to fill my library. Now the track attempts to play but after about 30 seconds of silence (with the playhead remaining at 0:00) it again skips to the next track. I think I may go back to the Genius Bar to bring this up again. It seemed to stymie them and Apple Support back when but maybe they have some more insight.

    • Kirk McElhearn says:

      It sounds like Apple has a corrupted file on their server. I’ve seen many corrupted files, and I don’t know of a useful way to let them know. You can contact iTunes Support, but they don’t seem to be able to do anything.


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