I noticed an issue a few months ago that songs that had been uploaded to my iCloud Library (a feature of Apple Music) were occasionally not playing on my iPhone. Trying to download or stream the song would result in my phone waiting a few seconds and then start playing the next queued song. The phone never threw an error and it always happened on the same songs.
All of my music is available locally on my computer, so I never saw the problem there. But out of curiosity I removed the download of one of the problematic songs, tried streaming and it failed on my computer. iTunes throws an error: "There was a problem downloading [song artist/ title] An unknown error occurred (-206). Please check the connection to the network is active and try again" After doing some digging I discovered that songs that had either been purchased from iTunes OR downloaded from iTunes Match and then uploaded to iCloud Library (instead of being matched by iCloud Library), will always fail to download from iCloud Library. In iTunes it can be filtered like this: Kind: “Purchased AAC audio file” OR “Matched AAC audio file” iCloud Status: “Uploaded” I was wondering if anyone else has experienced this issue? And if so, do you know how to force the song to upload?
And if anyone is willing, and I’d be very interested in knowing if you filter for those types of songs and remove the downloaded version, are you able to re-download or stream them? PLEASE BACKUP YOUR MUSIC BEFORE TRYING THIS — in my case, if I had not had a local backup of my library I would have lost these songs. Some example images of the errors: