7 Replies Latest reply: Feb 8, 2014 12:58 PM by CarsonsPlanet
e2photo Level 2 (165 points)

So this note has two pieces to it, one related to iTunes Match and the other is Sonos Play 5.   First an observation about the iTunes Match repeating problem.  I wanted to start using iTunes Match for a couple of reasons so I started to run it. It went through Step 1 and Step 2, started Step 3, stopped and restarted on Step 1. 


So I was reading trying to find a solution in the Apple Support Community.  Some suggested that there was a corrupted song in the library so I went back to watch to see if I could catch when it left Step 3 to go back to Step 1. I was not really able to see exactly were it was reverting back to Step 1. 


I then discovered ajlewis1851 note about reset Match, Store and the computer (https://discussions.apple.com/message/20530276#20530276)


I also discovered a song that was not in my library so I deleted that from the library as well.  Neither of these seemed to work and it was back repeating itself.


I left Match running while I was doing more searching and I discovered the thread about gating the upload speed as the upload speed might be the problem.  Well I spent a long time trying to figure out how to slow my Airport Extreme Base Station down and then I noticed that Match was uploading between 2-15 files before it would kick back to the beginning and the total number of files to be uploaded was slowly decreasing. 


Low and behold after quite some time, Match finally finished and said it was done!  This has to be some serious bug in Match, but eventually it got done.  Not sure whether the two steps before helped or not.


Now to the beginning of the story.  I started down this path because I was setting up a new iPod Touch to serve as controller for my new Sonos Play 5 system.  Everything seemed to work fine with Pandora and I was very excited. Synced a few playlist from my iTunes library and for many of the songs there was the dreaded ‘unplayable icon”-circle with a line through it!  Did some additional searching and discovered that the iPod Touch to Sonos Play 5 was only possible with DRM songs.


This is an aside.  It is necessary to place this discovery against my experience of playing my iPod thru a Sonos iPod Dock without having to worry about the DRM status of the music.  My disappointment was nearly overwhelming.


But Sonos recommended a strategy of iTunes Match to remove the DRM from the songs in my library.  Hence, my need for iTunes Match from the beginning of this story.  But this is not a very clean solution.  Even after one has done the iTunes Match, it is necessary to find all of the ‘Protected AAC audio files’ in your library, delete them and then download the ‘Purchased AAC audio files’ from the cloud.  (https://sonos.custhelp.com/app/answers/detail/a_id/626) and Apples directions (http://support.apple.com/kb/ht1711)


There are of tricks in doing this ‘Protected’ to ‘Purchased’ transition.  When you select Music in your library, and then right click on the top bar above the music you can select additional columns to be shown. Select ‘Kind’ and you can see which music is protected vs purchased.  You can sort this column, thus bring all of the ‘Protected’ files together, select them all and with one right click delete them!  (I very very strongly recommended you have a couple of backups of your library, just in case and there is a small box in the dialogue about deleting them from the Cloud as well---MAKE SURE THIS BOX IS NOT SELECTED). Much to my delight, in the ‘Cloud’ column, you are presented with the choice to download the ‘Cloud’ version (now DRM free).  As best as I can tell, one has to download each song from the Cloud individually. My fingers were very tired after millions of clicks.  I did a few at a time so it took me the better part of a day to accomplish. 


I was very excited because I now had DRM free music in my library (I figured this would solve the problem).  I connected the iPod Touch to the library, choose not to sync my playlist so all the playlists from the iPod Touch were removed and then reselected the playlists of interest and had them placed back on the iPod.  I ejected the iPod and tested the playlist on the Sonos.  Much to my surprise, the unplayable songs were still unplayable!!! 


I deleted the Sonos App and reinstalled it (Did not work). 


I deleted the playlist from the iPod Touch, and resync it to my library (You really don’t want to do this as it also deleted the playlist from my library!)  Fortunately, I had one of those backups.


I then sync another playlist to the iPod Touch.  This second playlist was the complete album from which two songs were placed in the original problem playlist.  Much to my surprise, all of the songs from the album were fine, EXCEPT, the two songs that were unplayable in the original playlist.


I finally came to the conclusion that something had been stored on the iPod during the initial sync with the DRM containing music that prevented the non-DRM music from working properly.  With a deep breath, and only after I disable the iPod Touch connection to iCloud (in a couple different places), I then went to Settings > General > Reset > Erase All Content and Settings and ran it to restore original factory settings. It was plugged into a power source.


After setting the iPod Touch up again, I reconnected it to my iTunes library and moved the problem playlist over that contained several unplayable songs.  IT WORKED!  All the songs were playable.



  1. 1. If iTunes Match keeps repeating steps 1 and 2 watch carefully to see if the number of songs to be processed is changing for the better.  If yes, at least in my situation, it completed the process, but it took much longer than I believe it should have.


  1. 2. My suspicion is that if you have installed DRM protected songs on an iPod Touch, the Sonos recommended solution will not work as stated.  Interestingly, it did seem work on my iPad and 4G iPhone. 


Addendum: I have discovered a few songs where the Sonos recommended solution did not work on the iPad and iPhone as well.  Several are from the Madonna.

  • CarsonsPlanet Level 1 (0 points)

    I have an iTunes library and have gone the Sonos route.   Half of my iTunes library won't play on Sonos due to Apples copy protection. Can iTunes songs be re-configured to play on Sonos? If so, does anyone know the steps needed?

  • e2photo Level 2 (165 points)

    You have to use iTunes Match. Then you have to delete the old DRM versions and download the new versions.  See my note above.  Make sure you have a backup

  • Michael Allbritton Level 6 (16,785 points)

    This topic has been discussed in-depth on this forum.


    Long story short, not all eligible songs in the iTunes library will "match." Some will be uploaded, or will retain their original iCloud Status of "purchased." If they are "purchased" or "uploaded" they cannot be upgraded to DRM-free tracks via iTunes Match. To see the status of the tracks switch to Song view and pull down View > View Options and select "iCloud Status" then close the small window. You can now sort on this column, find all the "matched" tracks that have been bought from the iTunes Store, delete them from the library and download the DRM-free versions. You can also use the tips in this Macworld article: http://www.macworld.com/article/1163620/how_to_upgrade_tracks_to_itunes_match_fa st.html.


    FYI, to download more than one track at a time, highlight the tracks you want to download, right-click and select "download."


    For the tracks that are "uploaded" or "purchased" the only way to convert them to DRM-free is to burn them to an Audio CD and re-import them to the library.

  • CarsonsPlanet Level 1 (0 points)

    Thank you for these pointers.  I will use them.  -Tony

  • Michael Allbritton Level 6 (16,785 points)

    You're welcome.

  • CarsonsPlanet Level 1 (0 points)

    I'm signing up for ITunes Match to begin the unlocking process and have a related question.....


    Since recieving an IPad a few years ago, I've been purchasing tracks mostly through the IPad without using iTunes on my Windows PC.   The IPad became my main device for buying and playing songs.


    It appears that Match is purchased through ITunes running on a PC or Mac and Match will run on the PC, not the IPad.


    Since much of my music library is located on the IPad rather than the ITunes PC where Match will run, will I need to download tracks to the PC on order to use Match on them?

  • CarsonsPlanet Level 1 (0 points)

    Well.....It is now working....... Including converting locked tracks located on the IPad library into unlocked 256kbps tracks playable by Sonos...


    Used these steps:


    1. Signed up for ITunes Match using ITunes on a Windows PC
    2. Let Match do it's thing with 700 or so tracks
    3. Followed the procedure in the link above to create a smart playlist of tracks with bit rates less than 256kbps
    4. Using the smart playlist as a guide, I deleted or download tracks not appearing in Sonos on the PC. Then, refreshed the Sonos music library and confirmed these tracks now available and playable by Sonos
    5. On the IPad, for tracks that were grayed out in Sonos, I deleted and re-downloaded the tracks using the Music app (swipe right to left on a track to delete it)... then got into Sonos on the IPad to confirm the tracks no longer grayed out.


    So... I'm now happy.... I like the Sono system of WIFI streaming which is very flexible and produces decent sound quality, but did not realize until after buying the Sonos bridge and two Sonos speakers that older ITunes songs would not play in Sonos due to DRM locking.  So, will now work through the library of locked tracks converting and re-downloading.


    Thanks again for the pointers on this question.