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Hands on with iTunes Match: Frustrating, but rewarding

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Apple (s aapl) officially launched iTunes Match on Monday, and things did not go entirely smoothly. I managed to sign up, and take the service for a test ride using a sandboxed segment of my iTunes library to see how it would handle iTunes purchases, ripped tracks and anything else I could think to throw at it.

A tale of two iClouds

I have a respectable library of around 15,000 songs, or about 100 GB of music from a mix of iTunes and CD purchases. With iTunes Match, I decided to ease into things using an account that has a respectable number of iTunes Music Store purchases, but on a machine that started off with zero ripped tracks in its music library.

While the activation of iTunes Match on this account from this particular Mac was rather quick — since the library was small — it wasn’t painless. After activating one of my iOS devices, I noticed right away that a little over half my music wasn’t added to my iTunes Match iCloud music library.  I made the mistake of assuming that iTunes Match would add my purchase history to my Match library, when it actually just uses your locally stored iTunes content. In the end, iTunes Match did recognize all of my iTunes music (once it was all downloaded to the computer I was using), but it would be in Apple’s interest to clarify this point.

Adding ripped music to iTunes Match

About 20 percent of my music library comes from just one artist: the Grateful Dead. I took the first ten albums in the infamous Dick’s Picks series and ripped them to my Mac’s iTunes library to see if I could have them matched.  iTunes Match performed well (assuming that’s because all the albums are available in the iTunes store), and started to match my ripped tracks as soon as they were added to my local iTunes music library.

I also added music I’d ripped previously by dragging the files to my iTunes library. As I was doing this, I checked the iCloud status of each track using the iCloud Status column, which you can enable in the View > View Options… menu.  Valid iCloud Statuses include Waiting, Error, Removed, Duplicate, Ineligible, Matched, Uploaded and Purchased.  You can create a Smart Playlist to keep track of which of your tracks fall into which iTunes Match category, as pictured above. Note that “Purchased” tracks, which are bought through iTunes, don’t count against your 25,000 song limit.

As each music file was added, I watched the status change from ‘waiting’ to ‘matched’.  This was the outcome I was hoping for. Six of the ten albums I matched has one or more tracks not matched, but they were uploaded instead, and thus still available via iCloud.

Uploaded not Matched

I tried everything to get iTunes to match all of my music, but there are some music files that it flagged as ineligible.  These are files that are either larger than 200 MB in size, have DRM from another music store or account, or were ripped at either a lower bit rate or to a format that iTunes doesn’t recognize.

To try to reduce ineligible tracks and increase matched vs. uploaded ones, I tried re-ripping problem songs from their original CDs to a higher bit rate. Despite my efforts, certain songs (which were available in the iTunes Store) just wouldn’t match. Hopefully the service’s ability to match tracks improves over time. In my opinion, 11 out of 189 songs being uploaded rather than matched isn’t a very good ratio, especially since the high bit rate of matched tracks is such a selling point of the service.

Missing Album Art

One last observation was that my album artwork wasn’t making the leap to the cloud immediately.  I’m kind of fanatic when it comes to album art, so at first this was troubling, but as time passed, I noticed that some of the covers started appearing.  I probably just need to be a little patient as iTunes Match catches up with demand. It’s good that Apple is prioritizing music uploads over artwork, too, if it comes down to a choice between the two.

Deleting, then downloading matched music

I recall a time when you could pay a company to rip your music collection for you. Apple’s iTunes Match is sort of like that, in that it takes your existing collection and provides you with a better, more usable version, which is exactly why I wanted to delete my source library and rebuild it using Apple’s higher-quality cloud-based tracks.

To test out how it would work, I went to a single album that had all of its tracks matched in my iCloud library, and deleted them.  I was careful not to delete the music from iCloud, too. Rather, I deleted the music from my local iTunes library without ticking the box next to “Also delete these songs from iCloud.”  The music was not actually removed from my library, but the status of the tracks I removed changed to reflect their presence in the cloud but not in local storage. Upon re-downloading, all of my 128 Kbps music files had been replaced with a collection of 256 Kbps music files.

Two conclusions

If your library is composed of mainly iTunes-purchased music, then I think you will enjoy what iTunes Match has to offer. Beyond simply keeping your music files in the iCloud, you’ll also be able to manage and share a set of playlists. This is a value-add feature that you can’t get by just downloading your previously purchased music from the iTunes Store. Plus, if you have a lot of legacy iTunes tracks with DRM, this is a good way of getting rid of that protection without having to pay per track to upgrade with iTunes Plus.

If, on the other hand, you have a substantial music library built mostly through ripping, then you may find yourself having to do a significant amount of pruning to get it in good enough shape to take full advantage of iTunes Match. After getting past the initial ordeal, however, I think most music fans will enjoy the cloud-based convenience features that iTunes match has to offer.

24 Responses to “Hands on with iTunes Match: Frustrating, but rewarding”

  1. John Doedoe

    With pleasure I PISS ON STEVE JOBS GRAVE!!! I tunes is such an annoying idotic wortless program. I poop and pee on Steve Jobs his grave when I get the chance to be in Alta Mesa. I will film it with my Iphone and upload it to youtube. I AM REALLY SERIOUS I AM GOING TO DO THAT!!!

  2. I have encountered a similar situation to others in that the majority of an album will ‘match’, yet one or two tracks from the album do not. They were ripped at the same time from the same CD, the length matches the one I see on the iTunes store, the track name and artist also appear identical, so it’s very odd.

    Hopefully this will improve going forward.

    One thing that I really don’t like is the ‘purchased’ music videos constantly showing up on the iOS device.
    Like many others I took advantage of the free Christmas offers (just to check them out) and then promptly deleted them from my library…however, these now appear constantly in the “Videos” app on the iOS device (with the cloud icon to allow a download).
    I’ve managed to hide them from my purchase history in iTunes, but this doesn’t seem to affect what appears on the iPhone.

    I know a lot of people want the option to manage their purchase history (especially with the amount of free throwaway apps out there) – so I’m hoping Apple listens and implements such a feature soon.

    • Actually I’ve been a little dumb with this one! You need to hide it from your purchase history, and also make sure to delete from the library completely (which somehow I’d missed first time around! :))

      One other note for iTunes Match users…
      I have two machines (a Windows 7 desktop and a MBP). I have historically synced my iPhone with my Windows desktop because that’s where the library was maintained (even though the files themselves are on my NAS box). With iTunes match it’s no longer necessary (for music at least), since the playlists and library content is available on all devices (finally an easy way to keep them in sync!).
      However, I often encode TV shows / videos and have to sync those via iTunes. I figured I’d change the primary sync computer to my MBP (thinking that it wouldn’t touch my music given that it is now handled via iTunes match). Unfortunately this was not the case, it wiped out the music I had on the phone and given that I had around 2000 tracks on there (from various albums/playlists) it’s an absolute nightmare to re-select them all manually on the iPhone.

      So for now I’m reverting to a manual sync from my primary computer again until I have more time to play with this feature (and until my entire library has finished uploading).

      Of the 20,000 tracks in my manually managed library, around 4,500 need uploading. A lot of these I’ll probably purge anyway (duplicates etc.) so this will reduce.

  3. I was hoping I could go to click on a music icon and see a list of my songs and play from there. This would be more like Google’s cloud. I can’t install iTunes on my work computer.

  4. I ran ITM on my collection of about 7000 tracks, and it matched 2800 and uploaded 4200. The weird this though is the hiccups. In some cases an entire album wasn’t matched–that seems normal, the album probably isn’t in iTunes. But I was looking at a recording I have of book one of Bach’s Well Tempered Kalvier (Edward Aldwell, pianist) It’s two CDs, 48 tracks. 47 of them matched, but for some reason it had to upload the Prelude in E-flat Major.

    The whole disc was ripped at the same time with the same settings. I have lots of other instances where albums were only partially matched.

  5. Mitesh Gandhi

    My iTunes Match worked fairly well. However, I have a lot of songs that are in ‘Uploaded’ Status and i wanted to know how i can change them so they become ‘Matched’. I changed around the tags for the Name, Artist and Album, and then deleted the song from my library and iCloud, and then added it back to the library (with the new tags). When I ran iTunes Match again, it still said Uploaded. Is there anyway to get it to Matched?

    • I am in the same boat as you. As I understand it, it has nothing to do with the tag, and everything to do with the rip. Meaning iTunes Match did not find a match for the digital ‘signature’ of the music file in your library. Think of it like Shazam or SoundHound. I have tried re-ripping the “uploaded” files again at a higher bitrate, and it still flagged them as “uploaded”.

  6. All my music is ripped from CDs I own. I don’t want iTunes Match. I don’t want to see it in my iTunes sidebar. How can I get rid of it? I don’t want iCloud. I think Lion is ugly and backwards. Apple is really forcing things on me that I have no interest in. I’m actually planning on buying a windows machine instead of getting a new MBP, and I’ve owned Apple since 1978, including an original Mac from 1985.

  7. Dennis Becker

    How does iTunes Match handle modified ID3 tags? I frequently change the genre of tracks (because I use more fine-grain categorization), and most of my playlists are smart lists depending on the genre. Will iTunes Match reflect these changes or go I get the original ID3 tags on other devices?

  8. Geoffrey, I have a similar situation. About 50% of my music collection is Grateful Dead (some commercial albums, but many more downloaded from the live music archive.) I’m finding that iTunes Match is flagging many many of my downloaded Dead songs as duplicates. Did this happen to you? If so, how did you solve the problem?

    • So far, I have not been attempting to ‘match’ such musical treasures. But I have run into one duplicate when trying to resolve a uploaded vs matched issue in my Dick’s Picks collection (#14, Morning Dew). On the same album, there are two versions of the same song which both have approximately the same length. I have not yet figured out how to bend iTunes Match to my will, and force it to accept the reality that while they may be the same “song”, they are in fact two different tracks.

      BTW, if you check the status of each of the files you are matching, you will likely realize that they are all being uploaded, and not matched. If they are being “matched”, I would listen to a few of them on a device other than the one you matched them from, and see if they are the same music file you thought they were.

  9. I see the same reports across the tech blogosphere but I agree with Richard that some important questions remain unanswered. Mine is the following:
    If you choose not to renew iTunes Match, what happens to the gazillions of high-quality recordings matched from my not-necessarily-too-legit collection that I just downloaded to my very private hard drive? Can I simply keep it, forever?
    Are we talking about a legal path to amnesty for $24.99? A digital music laundering scheme made legal by Apple? Man… I wonder how they convinced the labels to go with that…

    • I believe they gave the industry $100M up front in licensing fees. And if 200M Apple users pay $25/yr for the service, that would be a potential $5B/yr revenue stream. If someone offered me a way to make that much money off of music that was already sold once before, I would listen.

  10. Richard Evans

    Here’s the question I haven’t heard an answer to yet. If

    a) I like to play random selections from all of my music (over 2,000 tracks), and
    b) I’m using over 90% of my device’s memory, and
    c) I do not have an iPhone or other cell service

    Will the upgrade to higher fidelity tracks cause a memory crash, or will the higher fidelity tracks only play when I’m connected to WIFI? Until I fully understand the details of this iCloud process for times when I can’t connect to the cloud, I’ll have to keep my $25. I wish some journalist would really dig deep on this issue.

    • Your “on-device” music library will be replaced when you turn on iTunes Match on for that device. So to start, you will have zero music on the device. So no crash. Also, for your “on-mac” music library, it will not automatically replace the music you match, with the higher bitrate version. It will keep the original music file on the mac. If you delete the music from your mac, it will then download the higher nitrate version. You can manually download songs onto your device or Mac, or it will download songs as you listen to them.

  11. Nice article, but I disagree with one thing. If most of your music was purchased from ITunes, paying for Match may not be a good idea. Music purchased from ITunes is/was placed in the cloud as part of the ITunes upgrade of 10.5 (not 10.5.1 as required for Match). The Purchased feature of ITunes, which puts your purchased music on the cloud and makes it available for download to all your OS devices, has been available since the launch of 10.5 and OS 5 a few weeks ago. If all, or even most, of your tracks have been bought from ITunes, you might consider updating to the latest version of ITunes and OS 5, and passing on Match.

    • Shameer Mulji

      Thanks for saying exactly what I was thinking. All of my music is purchased from iTunes. What advantage do I have for using iTunes Match? Sounds to me like none.

      Sounds to me it would be a much better experience if they merge iTunes in the Cloud with iTunes Match. That way you don’t pay anything if your content is purchased from iTunes and only pay for content not purchased from iTunes – just like Amazon’s music service. Nice & easy to understand.

  12. Peggy Berk

    My Match went very smoothly – and very quickly – once i figured out what all the little icons mean…. I too have songs purchased from the iTunes Store marked with a slash over the cloud telling me that they didn’t upload – but if you click on the icon, it tells you that the song is already in your cTunes library and I have no purchases not downloaded. I can only guess that Match attempts to automatically move your “purchased” list into your cloud when you subscribe to match and that these songs do not have to be uploaded from your computer. It is weird though how just some of my purchases were marked this way and not others.

    Stranger yet – I also got an icon telling me that I could download a handful of other items – some were items I had previously downloaded, but more interesting most were items I had chosen not to download from the free Holiday Sampler iTunes gave away last year on Facebook…

    The whole process was really smooth and really fast and was updating my iPhone and iPad on the fly as the Match was happening… but I sure could have used a guide to Match’s icons…

  13. ” iTunes Match performed well (it may help that all of the albums are available in the iTunes store)…” Um, if it’s not in the iTunes Store, how the hell do you think it’s going to match?

    • I can see where Apple looses the right to sell a song to ‘new’ customers, but retains the right to host a digital copy in the cloud for ‘previous’ customers. Otherwise if Apple does not renew a contract with a particular record label, all of your music that you legally purchased would be gone.

      So there may be two different repositories of music in Apple’s music library. Ones they can sell, and ones they cannot sell. I just assumed that if they could sell it, they can match it. That is what I was thinking at least.