Updating your iTunes songs to the higher quality using iTunes Match

So I have turned on iTunes Match, as I’ve mentioned in several other posts here. Apple has made an attempt to give a good description of what the service is and how to use it – check this out from them… and then there is even more here “Learn More About iTunes Match.” They even have a nifty “Understanding the iCloud Status Icons

There are gaps though. I consider myself a pretty good reader and I consider myself someone who digs around for answers – more so than the average person trying to figure this stuff out! For instance I had an icon show up in my iTunes Library that is not listed on the above page. Another question i had was how to get the better quality file from iTunes Match that I had read about in all the advertising.

I had to dig around on the web to find an answer. I still can not find the answer on Apple’s web site. CNET gave me the answer. Follow along here and I’m going to go a bit more into depth.

Apple told me that iTunes Match would upgrade the quality of all those songs I recorded into my laptop from all my old cassette tapes. I have a ton of tapes that I simply put into the old tape deck, hooked an 1/8inch cable to RCA plugs, then pushed record on an audio program and proceeded to record all those old tapes – TOOK FOREVER! Plus at the time when I did it I made the choice to save the files as mp3 files. (I was thinking – save space and it’s about the same quality sound) Well, when I read that Apple would match those old mp3 files and upgrade their quality to the files they sell in the iTunes store, I liked that idea! I liked it even better when I realized that I would be able to keep those files in a year if I choose to not pay for iTunes Match again! Plus many of my tapes were WELL worn out – so the quality of sound coming into the laptop was questionable many times! But at least I had a digital copy of my tapes and I could listen to them from my iPod. I was happy, was being the key word here! So let me give you the short version….

  • MP3 files recorded from old worn out cassette tapes that barely played at times
  • Upgraded to 256-Kbps AAC DRM-free quality
  • I keep the better files at the end of the year!
  • SCORE!

So, like I said, I signed up. Took two days for Apple and my laptop to upload and match songs. (Short in comparison to Google Music’s 2 weeks!) Now I want my upgraded songs! Here’s how I did it…

We will look at one of my my cassette tapes that I had worn out so you get the picture of how this works.

First thing I want to bring up here is that when I knew I was going to turn iTunes Match on… I went to my iPad and deleted all the songs off my iPad. I did the same thing with my iPhone and iPod Touch. I had a ton of songs on there that were “Just in Case” songs. You know… the ones that I “MIGHT” want to listen to but probably never have or will (like at the end of an album – I mean with 6 kids when do I ever get to listen to an entire album?!) So on my iPad every time I listened to a song I was automatically downloading the newer, better quality file from the Cloud. So everything below here is simply so I could get the better quality file on my laptop and have a permanent copy of it on my hard drive.


On my laptop, in my iTunes library, I had to…

  1. select the songs that I knew iTunes had Matched,
  2. delete them from my iTunes library but keep them in the Cloud
  3. re-download them
  4. Enjoy the better songs!


STEP 1– So here is a screen shot of my album…Notice that some of the songs under iCloud Status say Matched and some simply say Uploaded. Why some songs on this album got Matched and some didn’t is a question for another day.

Take a look at the bottom two songs – You see that these two say Matched – that means iTunes has a better quality file in the Cloud waiting for you. Look over in the rectangle – you can see that Track 9 is a MPEG audio file. Track 7 is a track I already downloaded and updated, that’s why it says Matched AAC audio file.

STEP 2 – So the next step is to select the files that say Matched, then delete them from your iTunes on your computer but not on the cloud! Look below and you will see the pop up dialogue that appears when you hit the delete button, along with the check box that you DON’T want to have checked!

AGAIN – DO NOT DELETE these songs from the Cloud!

Then you can move these files from YOUR library to the trash. That pulls those old yucky files out of you iTunes library. You don’t want duplicates around wasting space.

I would not go empty the trash though. After downloading the better quality files you will be able to listen to the better files then listen to your old files – In my case it was very refreshing to actually make this comparison – HUGE difference!

STEP 3 – After deleting the files you will see that a Cloud, with an arrow in it, icon shows up next to those songs. That icon means the songs are in the Cloud waiting for you to download them.

Click on the little Cloud Arrow Icon….. Now the file starts to download and you see a little pie, progress icon that starts to fill up as the track downloads. It is a very fast process!

After the file downloads you can now see the songs will say Matched next to them and the file types have now changed…

Step 4 – Now all you have left to do is sit back and listen to your better quality files! Like I mentioned earlier – go pull those old version out of the trash and listen to the new version first then the old version. You will realize how much your were missing before. $25 bucks well spent I think if you have as many old file in your iTunes as I do!

By the way….

The screen shots I used in this post, you know… the ones with the pretty pink arrows and boxes…. were created in Skitch. Skitch is a free app for your Mac, Windows, iPad and a few other things too I think. It is a part of the service that Evernote offers. If you have not downloaded Skitch on your iPad especially, go do it now!

12 thoughts on “Updating your iTunes songs to the higher quality using iTunes Match

  1. I used to be recommended this website by means of my cousin. I am not positive whether or not this submit is written via him as no one else understand such specific approximately my problem. You are wonderful! Thank you!

  2. Thanks a million for these awesome instructions! Question for you: When you delete the original versions of songs, and download the higher quality versions from the cloud, does all your play count history get wiped out? I track play count data over time (for my own amusement, it doesn’t hurt anybody!) and while I really want the higher quality versions, not sure I can let go of that history! Thanks!!!

    1. Aaron,

      I don’t believe that your play count gets re-set. I played around with it a little bit on my computer. Check out my newest post for more info. I would say that you should try it with one track first though. This will let you experience exactly what will happen for your self.
      I hear you about the “history” though!
      Let us know how it turns out!

  3. Thanks Paul! Happy to report definitively that play count does NOT get wiped out when you download the higher quality version and delete your original song. How cool is that? I also found that altered song meta data sticks, too. Although I have heard of some issues with album art errors, I haven’t experienced it. I have officially replaced officially replaced over 2,000 songs without issue!

  4. I added some CD’s in my Itunes with skips, when you match them, and delete, uploud from cloud again, you keep receiving them with te same faults, Match is a fraud !!

    1. I would turn on the iTunes Match status and see what that says. It will tell if the song is being matched which means that you could download a better quality version from the cloud. It sounds to me like your song is not getting matched but instead is simply being uploaded, as is, to the cloud and you are indeed then just redownloading the exact same song again.

      Of course make sure that if it does say that the song is being matched that you actually delete the local, “bad version” before downloading the matched version from the cloud..

      iTunes Match works very well for me here.

  5. Hey Paul,
    A question for you. I also have a ton of tapes and was about to put them in the garbage when I thought about iTunes Match. I just recorded the first song on my laptop but the quality seems very poor (you know, the sound kind of comes and goes). After re-running/updating iTunes Match, the status of the song is “Uploaded” (even though the song exists in iTunes). Do you know if there’s any way to get iTunes to actually match that song? I wouldn’t want to listen to that song (and probably hundreds more) with such poor quality.

    1. I will need to dig back into the tapes that I did and check but I am pretty sure it has to do with having the correct length of the song, along with the correct tags …. Like Artist, Album, year and the such. If it exists in the iTunes Store though it should read Matched… That is when you end up with a better quality version. Then you can delete the file existing on your computer and then download the better version from the cloud.

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