Get started: Set up iTunes Match and upgrade your audio files

Wondering whether iTunes Match is worth $24.99 a year?  Assuming you have iTunes on your computer and a music library of several hundred or thousands of songs, ask yourself two questions:

1. Do you own an Android or iOS device (iPhone, iPad, or iPod touch)?

2. Are most of your songs at a bit-rate lower than 256 kbps?

If you answered yes to either one, iTunes Match is definitely worth at least a one-time investment to upgrade and clean up your music library. If you’re not sure about the bit rates for your songs, open iTunes and select your Music library.  Now right-click the column header and make sure Bit Rate is checked. Click Bit Rate to sort your library and check it out.

If you’re not up to paying $24.99 every year, we will show you how to quickly download upgraded files to your computers and devices, and store the shiny new library in the cloud using Google Play (née Music).

If you currently use Google Play, your first step should be to open Preferences and UNcheck “Automatically add songs uploaded to iTunes”.  This will prevent the upload of duplicate songs to your Play library.

More details on dealing with duplicates and working with Google Play are coming in Part 2.  Let’s start with signing up for iTunes and upgrading the audio quality of your music Library.

Subscribing to iTunes Match

You must have a valid credit card on file, and your subscription will automatically renew for one year periods until you cancel.  Open iTunes on your computer, choose iTunes Match in the sidebar, enter your Apple ID and password, and click Subscribe.  (Use the Apple ID that is associated with the majority of your music purchases.)

iTunes Match will then:

  1. Match the songs in your library with those in the iTunes Store.
  2. Create an index in the cloud to DRM-free 256 kbps AAC files that match the songs in your library.
  3. Upload any songs in your library that it could not match.*

* Apple fine print: 

Tunes Match works with libraries that contain up to 25,000 songs which are either (i) not currently available on the iTunes Service, or (ii) not purchased from the iTunes Service with your Account.

  • Songs with quality less than 96 kbps or that are not authorized for your computer are not eligible for iTunes Match.
  • Song files over 200 MB will not be uploaded to iCloud.
  • Songs containing DRM (Digital Rights Management) will not be matched or uploaded to iCloud unless your computer is authorized for playback of that content.
  • Songs encoded in ALAC, WAV, or AIFF will be transcoded to a separate temporary AAC 256 kbps file locally, prior to uploading to iCloud. The original files will remain untouched.

Upgrade your local files to 256 kbps

You now have two iTunes Libraries:

iTunes in the Cloud – All the songs that were matched, plus all of the unmatched songs that were uploaded.  The matched songs are AAC 256 kbps files.  Eligible unmatched MP3 or AAC files are uploaded at their original bit rates, other file types are transcoded to 256 kbps AAC.

Local iTunes Library – This contains all of your non-music audio content (e.g., podcasts, audiobooks) plus other file types for books, videos, photos and apps.  Your original music files are still there, and still at their original bit rates.

This is where the magic happens.  We need to identify the music that is eligible for upgrade: all files under 256 kbps that iTunes has marked as matched or purchased.  And thanks to Jason Snell and MacWorld, we can do this quickly with a smart playlist.

From the iTunes menu select File > New Smart Playlist
Click the dropdown boxes and select Bit Rate | is less than | 256
Click + to add a new condition
Select Media Kind | is | Music

Add a second set of conditions:

Hold down the alt/option key and click the + button (now an ellipsis)
Select Any of the following are true
Select iCloud Status | is | Matched
Click + to add a new condition
Select iCloud Status | is | Purchased

Your selection window should now look like this:

Click OK and name your new playlist “Upgradeable”

The new playlist should show all your files that are eligible for upgrade:

Now would be a good time to empty your trash, so you’ll have a clean can for all of the files you’re about to delete.  In order to bring the new files down from iCloud, you will need to delete the local versions.

  • Select all of the songs in the Upgradeable playlist
  • Hold down the alt/option key (shift key on PC) and press delete
  • Make sure that “Also delete these songs from iCloud.” is NOT checked
  • Click Delete Songs
  • Click Yes when asked if you want to move the files to the trash

Your upgradeable playlist should now show that these songs are available for download from iCloud:

To bring the files down from iCloud:

  • Select all songs in the Upgradeable Playlist
  • Control-click (or right click) and select Download

That’s it!  Make sure you have all the files you want keep before emptying the trash, and get ready for some serious cleanup in Part 2.