Ask the iTunes guy: iTunes Match

Kirk McElhearn
1 July, 2012
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Though Apple touts the ease-of-use of its products, figuring out how to get the most out of an application such as iTunes can be tricky. KIRK McELHEARN answers 28 commonly asked questions about how iTunes Match works and about general iTunes tasks such as tagging files, dealing with album artwork, working with playlists and more.


iTunes Match

Work with Apple’s $34.99-a-year music service 


Apple’s iTunes Match service compares the tracks in your iTunes library with those in Apple’s 20-million-song catalogue and lets you upload the ones it can’t match (you can upload a maximum of 25,000 non-purchased tracks).

And for the tracks it does match, you can download Apple’s copies to replace your own poorly ripped MP3 files from a decade ago. You can then access those songs via iTunes or your iOS devices whenever you want. Sounds simple enough, but there are dozens of questions you could ask about iTunes Match.

1) I have more than 25,000 songs. How can I prevent the matching of some songs and allow others to sync without removing the excess songs from my library?

Unfortunately, I’m in the same boat (something I lamented in an article last year). Apple offers no way to exclude certain tracks – if your library tips the scales, you won’t even be able to sign up for iTunes Match.

One (rather clumsy) solution is to select the tracks you don’t want included and change their Media Kind to Voice Memo (File > Get Info > Options). iTunes Match sees those tracks as unfit for duty (aka ineligible). But perhaps the best solution for now is to put your iTunes Match library on a second computer or create a second library just for iTunes Match purposes.

To do this, quit iTunes, hold down the Option key, and launch iTunes. You’ll be prompted to create a new library or choose a different library. Choose the option to create a new library. iTunes will open and you’ll have no tunes in your library.

Move to the Store menu and choose ‘Turn on iTunes Match’. You’ll be prompted for your Apple ID and password. Enter them and click OK and iTunes will switch on iTunes Match. Now open iTunes’ preferences, click the Advanced preference, and uncheck the Copy Files to iTunes Media Folder When Adding to Library option and click OK. This will prevent iTunes from generating duplicates when you follow the next step.

That next step is to choose File > Add to Library and browse for tracks that you want added to iTunes Match. When you’ve finished, choose Store > Update iTunes Match. The iTunes Match entry will appear in iTunes’ Source list under the Store heading and Match will run through its three-step program – gather information about your library, match your now-smaller library with tracks on the iTunes Store, and upload artwork and remaining songs (if the Store doesn’t have some of the tracks you’re matching).

Clunky, yes. Inconvenient, certainly. But it does provide a way to make your favourite tracks available to iTunes Match. Once you do this, you can then switch back to your regular library by quitting iTunes, relaunching it with the Option key held down and then choosing your old library. The tracks you’ve matched will still be available to other computers and iOS devices.

We sincerely hope that Apple will add a tag to iTunes to let you exclude specific files from iTunes Match.

2) If I switch to iTunes Match, how can I listen to my music on my iPhone when I don’t have mobile coverage? And how much data am I going to gobble up streaming my music to myself all the time?

Turn off cellular data so you don’t exceed your data limits with iTunes Match.

First let’s clarify: Computers can stream iTunes Match content, but iOS devices download it. So although you can listen to music on an iOS device while it’s downloading, iTunes downloads the entire file.

But unless you have a Wi-Fi or 3G data signal, you won’t be able to download music.

In general, however, you will use up a lot of data downloading and listening to music stored in the cloud. Just look at the size of any of your music files – that’s what you’ll be downloading. An hour of 256 kbps music, for example, takes up roughly 120MB.

If your data plan is limited, go to Settings on your iPhone and tap General > Network. Turn off Cellular Data to make sure you don’t accidentally use too much data. That will limit your iPhone to downloading music (and everything else) via Wi-Fi.

3) Many songs in my library are sold on the iTunes Store but have been uploaded rather than matched. If I change the titles’ spellings to match Apple’s, will that make the files match instead?

iTunes Match doesn’t match all the tracks it should, but not because of how you’ve tagged them. iTunes Match ignores the tags and looks at the music alone, creating an acoustic fingerprint to match against its catalogue.

So even if you change tags on your own – something I often do with classical music – this won’t affect whether songs match. Also note that if you match songs whose tags are incorrect, iTunes won’t fix those tags for you.

 4) Do I have to download each song to my Mac individually by clicking on the iCloud symbol next to the song or is there a download-all option somewhere?

Just select the files you want to download – a few songs, an entire album or your entire library – and then Control-click or right-click on the selection and choose Download from the contextual menu that appears. This downloads all the selected files. Naturally, if you’re downloading your entire library (or a fairly large chunk
of it), be prepared for the process to take a long time.

5) I spent a lot of time adding CDs to my iTunes library in either WAV or Apple Lossless formats. If I understand correctly, I will lose this quality level if I use iTunes Match. Is this correct?

Yes and no. iTunes Match doesn’t alter the songs in your library unless you choose to replace them. If iTunes
has matched a lossless track and you delete your master file, the version you re-download from iTunes will be 256 kbps. And if you download that track on another computer or an iOS device, it will similarly be 256 kbps.

Unmatched lossless audio files that iTunes uploads get transcoded to a 256 kbps AAC file first but, again, that doesn’t affect your originals. In most cases, 256 kbps AAC files are fine for portable devices – taking into consideration their limited storage space and the headphones or speakers you’ll be listening through.

So you might want to use iTunes Match to provide music to, say, an iPhone, but still use your Mac’s iTunes library when you listen via a stereo.

6) A lot of my older downloads are protected AAC files that are no longer available on the iTunes Store. How can I get these songs onto my other devices?

I, too, found that many songs I bought from the iTunes Store turned out not to match and were no longer sold on the iTunes Store. However, none of these were listed as ineligible and all of them were uploaded.

The only ineligible tracks are those at bit rates of less than 96 kilobits per second (kbps) and files larger than 200MB. So in your case, there must be another reason. Check the files by pressing c-I and looking on the Summary tab of the resulting Get Info window to see what types of files they are and what their bit rates are.

7) If I subscribe to iTunes Match, will my playlists be available on other Macs or iOS devices just as they are on my home computer?

iTunes Match syncs and displays your playlists on all the computers and iOS devices (up to 10 in total) on which you’ve enabled iTunes Match. However, if you have playlists that contain podcasts, videos or music videos, those playlists won’t sync (even if a playlist includes 1000 songs and just one music video). But all your music-only playlists should be available on your computers and portable devices.

8 ) I have many albums where iTunes uploaded one or more songs instead of matching them. Is there a way to get these songs to match?

Like you, I have many albums where just one or two tracks don’t match and many of those songs are indeed available on the iTunes Store. In some cases, it seems that certain versions – say, an older re-master – won’t match with a newer one. (This is definitely the case for certain Beatles songs.) It’s not clear whether Apple plans to provide a ‘retry’ option. For now the best thing to do is to delete the songs from iTunes Match and then try matching them again using your original rips (you did keep backups, right?).

While there’s no guarantee this will work, I’m sure that Apple is refining the matching algorithm and I hope things will improve over time.

9) How do you sync play counts and last-played info from your iPad back to your Mac with iTunesMatch turned on? Does this info sync wirelessly?

In theory, this information is supposed to sync – iTunes periodically updates iTunes Match, checking for new tracks in your library and downloading such information. You can force an update by choosing Store > Update iTunes Match from iTunes on your Mac. However, I have seen a number of reports of this data not updating correctly, so there may be some bugs that prevent this from working in all cases.

10) Will I be able to sync my iPod classic if I subscribe to iTunes Match?

No. iTunes Match works only with computers (Macs and PCs running iTunes 10.5.1 or later) and iOS devices (iPhones, iPads and iPod touches running iOS 5.0.1 or later).

However, you can still sync other iPod models directly via iTunes, as you have done in the past. Only the music located in your library will sync, though – in other words, songs in the cloud won’t sync from your Mac to an iPod classic. As a workaround, you can use iTunes Match to download tracks to the computer you use to sync the iPod classic.


iTunes libraries

Move your library and open multiple windows 


Working with the iTunes interface and your library can be confusing at times. These solutions should offer some clarity.

11) Is it possible to have more than one iTunes window open at a time?

Depending on how you use iTunes and the size of your screen, you may want to open multiple windows.

Yes. Double-click almost any item in the iTunes source list (on the left) to open it in a separate window. Alternatively, Control-click or right-click the item and choose Open In New Window from the contextual menu that appears. This works with the various libraries (except for the main music library), the iTunes Store, Genius and your playlists.

12) The hard drive on my MacBook Pro is quickly filling up. Can I move just my movies, TV shows and other non-music items to an external drive?

You can. Start by going to the iTunes folder in the Music folder within your home folder. The iTunes Media folder (or iTunes Music folder, if you’ve been using iTunes for a long time) contains many subfolders, which in turn contain movies, TV shows and more. Choose which of these folders you want to move and then copy them to the external drive.

After you’ve finished copying them, move the original folders to the Trash. On the external hard drive, select the copied folders, press and hold c-Option and then drag the folder to your iTunes Media folder; this creates aliases. As long as the external drive is mounted, any content you add to your iTunes library for those folders goes to that drive. You should quit iTunes before you connect and mount that drive. Once it’s mounted, relaunch iTunes.

13) How can I see which playlist or playlists contain a particular song?

If you Control-click or right-click a track, you can choose Show In Playlist from the contextual menu to see which playlists contain that track.

14) Is there a very quick way to tell which iTunes tracks have DRM and which ones don’t?

Indeed there is – with a smart playlist. While in your music library, choose File > New Smart Playlist and set the first pop-up menu to Kind and the second to Contains. In the text field, type Protected AAC audio file and save the playlist.

If you want to see all your files with DRM – not just music, but also videos and books – just type Protected for the kind.

Optionally, you can add the Kind column to iTunes’ display (press c-J, select Kind and click OK). After that, if you sort by Kind by clicking on that heading in iTunes, you’ll find all your protected tracks grouped together.

15) I have four user accounts on my iMac. What is the best way to let them all access my library and make playlists?

This scenario is a good example of where iTunes Match can be useful: It lets each user access all the music and create playlists. Since playlists get synced, you might want to create a playlist folder for each user and have them put their playlists in that folder.


Album art and tagging

Delete art, add custom text to tags and join tracks 


Tagging files in your iTunes library helps you find the music you want to listen to and lets you create smart playlists. And album art gives you a visual reminder of what you’re listening to.

16) What exactly are tags?

Tags include such things as the name of a song or movie, a track number or a genre. A number of other tags tell iTunes to do certain things, such as skip files when you’re playing music in shuffle mode. The Summary pane of a track’s Info window shows many of its tags.

When you buy music from the iTunes Store, it comes tagged with all the relevant information. And when you rip your own CDs, iTunes looks up the tag information online and adds it to your tracks. You’re free to alter the tags as much as you like.

17) Many of my songs segue into each other. How can I make iTunes play the segued songs together, even when shuffling?

The best way is to join the tracks when you rip a CD. To combine segued tracks, select the files you want to join and choose ‘Join CD Tracks’ from iTunes’ Advanced menu. iTunes places a bracket next to the tracks that it will join when you click Import CD. I do this manoeuvre often, especially for live Grateful Dead staples.

If you’ve already ripped the tracks, you can use Doug Adams’s free Join Together to join them. Be sure to read the instructions, as some of its functions are limited under OS X 10.7 Lion.

18) There used to be a ‘HasArtwork’ option for smart playlists. How do I get that now?

Create a smart playlist (File > New Smart Playlist) with Album Artwork in the first pop-up menu and ‘Is True’ in the second to see which tracks have artwork. To see which tracks lack artwork, choose ‘Is False’.

19) I like to add personnel and set lists to concert films, but the comments field is too small. Is there a way to add more information to video files?

As odd as it sounds, your best bet is to use the Get Info window’s Lyrics tab. It holds about 24,800 characters, which should be more than enough room for your needs. You’re free to add pretty much all the information you want in that tag.

20) How do I delete album art from a group of songs?

Select all the relevant files and press c-I. You’ll see an Artwork pane in the lower right corner of the resulting Get Info window. Check the box next to this well and then click OK. This deletes all the art – even if there are multiple covers – for the selected tracks.

21) Is there a way to save my place when I’m listening to really long radio shows?

Select the file from within iTunes, choose File > Get Info or press c-I and click on the Options tab. There you’ll find a Remember Playback Position option. Check the box next to the option and click OK.

Not only does iTunes remember where you left off, but if you sync that track to an iPod or iPhone, you can pick up from that point on your portable device as well. Each time you sync, your current place gets synced as well.


Playlists and more

Create helpful playlists to listen the way you want 


Playlists let you organise music in many ways. Rather than listening to an album, you can choose your favourite tracks by one artist or set up a mix of dozens of artists, all with a few clicks.

22) Can I combine several ‘favourites’ playlists so that they play together in iTunes?

I can think of two ways to do this. The first is to drag the playlists you want to listen to onto the iTunes
DJ icon in the source list; this adds their tracks to iTunes DJ (if you don’t see the icon, go to iTunes’ General preferences and check the box next to iTunes DJ).

This smart playlist can consolidate the many tracks you may have for an audiobook.

Another way is to create a smart playlist that contains those multiple playlists. Choose File > New Smart Playlist. In the resulting window, choose ‘Playlist’ from the first pop-up menu, ‘Is’ from the second and the name of one of your desired playlists from the third.

Click on the plus-sign button (+) to the right of that line and do the same thing again, adding a different playlist.

Repeat until you’ve added all the playlists you want. Before you click OK to save the smart playlist, make sure
to select ‘Match Any Of The Following Rules’ at the top of the window. Save the smart playlist, which will contain all the songs in the selected playlists.

23) I listen to a lot of plays as audiobooks. Is there a way to combine many small tracks into one so that there are fewer tracks for each play?

As a big fan of Shakespeare, I have recordings of all of his plays in my iTunes library. The easiest thing in
this case is to create a smart playlist: for example, ‘Artist Is William Shakespeare’, ‘Album Is The Tempest’ and ‘Plays Is 0’. As you play each track, it gets removed from the playlist, since the play count increases to 1.

Note that you need to change the files’ media kind to Music (select the files, press c-I and then click the Options tab and choose the Media Kind menu). Doing so puts the files in your music library so that you can use this type of smart playlist.

If you still want a small number of files, you can use Doug Adams’s aforementioned Join Together script to join tracks you’ve already ripped.

24) Can I copy a playlist and the songs it contains from iTunes to a USB thumb drive?

If you want to import that playlist into iTunes on another computer, first select all the songs in the playlist and then drag them to the thumb drive.

Next, with the playlist selected in the source list, choose File > Library > Export Playlist. Save this file on the thumb drive as well.

To import this playlist into iTunes on another computer, connect the thumb drive and then copy the music files into iTunes. Next, choose File > Library > Import Playlist and select the playlist file you exported earlier. The playlist will display in the iTunes source list, with all the songs that you added.

25) I use several playlists as background for meditation and find the short break between songs distracting. Can I avoid the break?

The tiny gap between tracks in iTunes can be really frustrating. Try turning on the Crossfade Songs option in iTunes’ Playback preferences. When you select this and choose a time in seconds, iTunes segues tracks, fading from one to the next.

If you have songs with portions of silence in the tracks themselves, you can alter the start and stop times within the Get Info window’s Options tab or use an external audio editor to alter the tracks permanently.

26) Is there any way to associate a single song file with multiple albums?

You can’t tag one song with multiple album tags. But if you created playlists for each of your albums, you could add one version of a song to each playlist.

The attached album name would be the same each time, but would appear as though it were from the album for which you created the playlist. But the track number will be whatever it is for the master file, so albums might not play in the proper order.

Make audio iTunes-friendly

27) I have audio files in a number of formats that iTunes doesn’t support – notably FLAC, Shorten and Ogg Vorbis. What can I do if I want to add them to iTunes?

The free XLD does a great job of converting most audio formats to something iTunes can handle.

A number of programs can convert audio files from one format to another, but Tmkk’s free X Lossless Decoder or XLD is our tool of choice, as it manages every audio file format we’ve ever come across, along with some we’ve never heard of.

Conversion involves choosing an output format and bit rate and then dragging the files you want to convert onto the program’s window or icon.

If, for example, you’ve bought some music in FLAC format and you want to listen to it in iTunes, you can use XLD to convert the files to Apple Lossless; since both formats are lossless, you’ll have exactly the same data in the resulting files. (Converting from one lossless format to another does not result in any change in quality.) And you’ll retain any metadata in the original files as well.

To convert your files, go to the General tab of XLD’s preferences and select Apple Lossless from the Output Format pop-up menu at the top. In the Output Directory pop-up menu below that, choose where you want to save the converted files.

If you wish to copy the new files to iTunes, select the Add Encoded Files To iTunes If Possible option near the bottom of the window. (To put the files in their own playlist, select Playlist rather than Library and create a name for the new playlist.) Now, in the Finder, just drag and drop your files to XLD’s application icon and let XLD do the rest.

Great iTunes AppleScripts

28) Could you recommend any cool AppleScripts for iTunes?

iTunes is extremely friendly to the AppleScript scripting language and Doug Adams offers a great selection of scripts in his Doug’s AppleScripts for iTunes ( Here are some of my favourites.

De-Genre. If you’ve attempted to choose music in your iTunes library or on your iOS device by genre and found countless related genre listings – Alternative Country, Alternative Roots and Alternative R&B, say – it’s time to fire up De-Genre. This script combines related genre listings into a single entry – Alternative, in this case. This in turn removes the other entries cluttering your library.

You can easily retag videos with the Set Video Kind of Selected script.

Set Video Kind of Selected. Those of us who routinely add video files to iTunes know that iTunes places them in the Movies folder. If they’re music videos or TV shows, you must edit their tags.

This AppleScript lets you dispense with such drudgery and instead edit the video kind, show name, season number and episode number tags for multiple files in one go.

Super Remove Dead Tracks. Are you annoyed by the exclamation marks (!) next to tracks in your iTunes library that are no longer available? This script takes care of the problem by removing those tracks permanently.

Find Album Artwork with Google. iTunes does its best to add album artwork to your music collection, but it can do so only for albums that are in the iTunes Store and are properly tagged.

Choose a track (or multiple tracks) sans artwork and then invoke this script and your web browser opens to a Google Images page revealing any found artwork for that track. Simply click on the artwork to reveal its full- size image and copy that artwork to the track.


3 people were compelled to have their say. We encourage you to do the same..

  1. Katie says:

    Hello! I can’t even get my computer to recognize my ipod! I don’t understand ANY of this. I had a Creative mp3 (my 3rd) that I loved and never had problems with.(till it stopped working anyway) My sister insited getting ipod touch that I can barely use. I hate this thing! I can’t even tell you how I got any music on it in the first place. I drag over what I wan’t to put on it, plug in my device and it still say’s Plug in device. IT IS PLUGGED IN. I really miss Creative.

  2. Ian says:

    A great place to find album artwork to use for your iTunes collection is at The quality of artwork is very good. For iTunes I recommend finding the album art at 600×600 and importing the album art for those ones you wish to use by doing this: 1) Find the album art you wish to use. Keep this page open. 2) In iTunes, highlight all the tracks from the album. 3) Right click and select Get Info. This will open up the Info tab for the whole album. 4) Click the full size album art from the site and drag it directly into iTunes to the Artwork box on the bottom right under Info. The image will fill this box and a tick will appear next to it. 5) Click OK and you’ve got yourself high quality album art for your iTunes collection! :-)

  3. asa says:

    I didn’t tag my kids harry Potter albums to “skip when in shuffle mode” and everything is up in the cloud. In shuffle mode on my iPad at work, Stephen Fry keeps popping up! If I tag them on my iTunes now is there a way to force it to replace/update the cloud?

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