It feels as if I’ve been waiting forever to finally write this review of Apple’s new iTunes Match cloud music streaming service.

Dear David,

This email confirms that you have purchased a 1-Year subscription to iTunes Match for $24.99 on 11/14/11. This subscription will automatically renew each year unless you turn it off no later than 24 hours before the end of your current subscription period. To cancel the automatic renewal of this subscription, sign in to iTunes with your Apple ID and go to your Account Information page.


The iTunes Store team

After signing up for the yearly service, iTunes took me into a three step process.  Step 1, seen in the screenshot below, took 2.5 hours to complete as “information was gathered” about my existing iTunes library.

Step 2: “Matching your music with songs in the iTunes Store” took a little over 2.5 hours to match — or not — 20,273 songs.

Here’s how my iTunes sidebar changed as Step 2 was matching my songs. The cloud with the slash through it means there is content — ironically, almost always an iTunes digital booklet — that is “not compatible” with iCloud.

“Step 3” uploaded artwork and remaining songs and took 12 hours.  Out of 20,273 songs I had in iTunes, 6,163 songs were not in iTunes.  That meant I had to wait a long time for those six thousand songs to upload before I could begin to feel comfortable rooting around iTunes Match.

I did as as iTunes instructed and I turned on iTunes Match in the settings for my iPhone 4S.  I was surprised to learn all my current music would be removed from my phone.

Here’s the new instruction on the music page:  “All music that has been downloaded or that is stored on iCloud will be shown.”  Okay, then.

Here are some of the album covers that began to download from iCloud and pop up on my iPhone screen.

While I waited into my second hour of uploading the six thousand songs, I decided to poke around a bit more in iTunes and found some new icons.  This “iCloud” icon with an exclamation mark tells you nothing — except that there’s a problem — and offers no retry option to fix the offending files.

I learned that a double “iCloud” cloud with a slash through it indicates a duplicate.  I haven’t decided yet how to deal with these duplicates, but I’m glad iTunes is giving me lots of informed choices on how to handle my local music.

After waiting for over six hours for this final iTunes Match step to finish, I decided to go to bed.  Here are a couple of screenshots from my iPad 2 I was able to capture as my music was being transformed into iCloud.

I love clicking on the single “Download All” button to bring all the songs on an album into the iPad 2 music player.

When I awoke, I discovered iTunes Match was finishing up.  After 18 hours, my musical transition into the Apple iCloud was complete!

I discovered 581 “lost songs” hosted in the iCloud that I had purchased in the past, but those songs had somehow become corrupted in the transition from one computer to another.  iTunes Match found those paid-for-but-orphaned songs and restored them to my iCloud library.  I clicked on the found songs to download them to my local copy of iTunes.

Over the years, I was smart to always purchase my music from iTunes.  That loyal, one-stop shopping paid off.  Apple allowed me to re-download my entire iTunes library at least three times in the past because of critical disk failures on my side.  In that re-conditioning of your entire iTunes library, some songs get lost in the mix because songs and artists and albums continuously appear and disappear in the iTunes songs library –and if you purchased a song in the past from iTunes, but the song was no longer available on iTunes for your re-download — you were out of luck.  You lost the song.  That’s the great thing about iTunes Match.  Once you prove you own the song, the song is yours in the iCloud.  Nothing messy can ever touch, or reduce, your library again.  It appears that iTunes Match remembers all my purchases from the past and allows me access, once again, to songs I purchased — but lost — in the miasma of song rights management.

iTunes Match also found a mess of duplicate songs.  Sometimes, due to technical glitches and other bothersome computer anomalies, songs get re-purchased or copied, and I have to deal with the conundrum of what to do with the duplicates.  Do I just remove them from view or remove the actual file, too?  With iTunes Match enabled, I can now confidently just remove the file.  If I need a copy of the copy, I can pull it later from my iCloud library.  Now I just wish there were a simple, and safe, way to automatically remove all duplicate files and to “download all” songs that are in the iTunes Match cloud.

Once iTunes Match has you — they own you — because if you cancel your yearly subscription, you can say good-bye to your preserved, matched, music library in the cloud. Apple effectively made us all clients for life because we want the simplicity and we crave the universal sharing between connected devices.

Even though the initial iTunes Match setup cost me 18 hours of my life, iTunes Match is a brilliant way to guarantee the safety of your musical library and purchases — as long as you keep paying Apple’s yearly dunning.  We’re now in the era of renting our music instead of purchasing it outright and iTunes Match is a wonderful step in helping us realize that next horizon in musical enjoyment.

One thing I can’t figure out is how many songs I have in iTunes Match that count against my 25,000 song limit. I thought that iTunes-identified songs didn’t count against that limit — only songs that had to be physically uploaded to the server counted against you. If you know the answer to that count question, please let me know in the comments stream below.

UPDATE: 35 Minutes After Publication.
Here’s a clunky way of finding out your split between “Uploaded” music and “Matched” and “Purchased” music.  iTunes Match counts Uploaded and Matched songs against your 25,000 song limit.  Purchased music are songs you bought via iTunes.

Using iTunes, go into — VIEW | View Options — and enable “iCloud Stats” that will tell you which songs are Uploaded, Matched and Purchased.  Then, click on that column and iTunes will reorder the songs based on their iCloud status.  Then, SHIFT+CLICK on the first “Matched” song and SHIFT+CLICK on the last “Matched” song and iTunes will report how many items are in that list.  Repeat for “Uploaded.”

Out of 21,352 items in my entire local iTunes Library, 4,302 are Uploaded; 5,820 are “Matched” and the rest are “Purchased” or “Not Eligible” for iTunes Match.  So I officially have 10,122 Uploaded and Matched songs counting against my overall 25,000 song limit.


  1. Hi Gordon —

    That link confirms what I know — what I want to find out is how many songs iTunes Match is currently counting against my 25,000 song limit. I can’t find that differentiation between iTunes matched and uploaded.

  2. UPDATE:

    I figured out a rough way of learning how many songs you have that actually count against your iTunes Match 25,000-song limit. I updated the article above to reflect my findings.

  3. UPDATE:

    Here’s a terrific tutorial to explain how to get your local non-256kbps upgraded to iTunes-specific 256kbps songs:

    I followed the instructions and replaced 2,334 songs. Worked like a dream! Super happy with the upgrade in sound for the price of my subscription.

  4. I don’t have many songs, but I signed up for iTunes Match today just to see what would happen. I was very surprised to see so many songs that I’d “lost” over the years after buying them showing up in my account again. Apple gave me back over 150 songs that were associated with my Apple ID that I didn’t have on my current computer and that I’d just written off as gone forever. Now I have all my previously purchased songs back! Paying a dollar a song to restore those songs would’ve cost me $150 — so $25 a year is a bargain for the first year and five years after that!

    1. I’m so glad you signed up, Janna! Now all your music is on all your iOS devices again without you having to worry about where and how your music has gone missing.

  5. I’m loving iTunes Match. Amazon and Google are now uploading the updated 256kbps songs.

    I do wish we had iTunes Match as part of iCloud so we could manage our music — and stream it — from any computer. I’d pay extra for that feature.

  6. Going to sign up straight off. This is part of iCloud or not a part? Love the idea of having lost songs returned. As it should be.

    1. That’s interesting question, Anne, because it is confusing. The screenshots say iTunes Match is part of iCloud — but if you login to — there’s no iTunes Match there waiting for you. It’s confusing.

  7. If you keep the duplicate songs they will count to the 25,000 limit?
    And what if you choose to delete them?

    Another question:
    If I delete a song from the cloud will this remove the song from the limit count?

    1. As I understand it, Bert, duplicates will count against your 25,000 song limit — though I’m not certain why you’d want to include exact duplicates in iTunes Match. If you delete the non-iTunes purchased songs, they will disappear forever if you choose to delete the song file and “remove it from iCloud.”

      If you purchase a song from iTunes, it doesn’t count against the 25,000 song limit. If you remove a matched song from iCloud then yes, as I understand it, your song count would be lowered.

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