iTunes Match keeps repeating and Sonos Play 5!

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/thread/4572941?answerId=20530276022#20530276022)

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.

LESSONS:

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.

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.