16 years ago, I signed up for iTools and got my Apple ID that I use to this day. 3 years later, I started buying music from the iTunes music Store. 2 weeks ago I noticed that music I had purchased wasn't playable any more. Grrrr.

I started getting errors telling me songs that I purchased with DRM on them (i.e. Not iTunes Plus songs) were not playable because they had not "been purchased with your Apple ID". I haven't done a thorough analysis of my library, but there are likely hundreds of affected songs.

I checked some other known files and saw the same things with them too. My next destination was Apple support. I've used their chat system before to great success so I started there. 2 hours and a couple of transfers later, they wanted to schedule a call for the following morning. That call lasted 2 hours and got me bounced to 4 total reps.

Here's the "solution" we found:

• Download files to my computer for the affected songs
• Delete the songs from iCloud library, but keeping the files on disk
• Import those songs into iTunes
• Add the songs to iCloud

Again, I don't know how many songs are impacted right now. But it's a lot. And doing this means I lose play counts for up to 13 years of a given song's history. That's the biggest bummer for me in all this (and the time I will have to spend actually doing the work). So 4 hours of discussion with Apple and I just have more work ahead of me.

What I believe happened, is that the music that I had purchased on the store, and later converted to iTunes Plus, is still appearing to my Apple Music account as non-iTunes Plus. That's annoying, but fine. The real problem is that my Apple Music account is one that I share with my wife and she is the one that started the subscription. One of the troubleshooting steps we went through on the phone was for me to log out and then log in as her. The songs then played just fine.

One last thing that I checked is the backup I have of all my music, from when my iTunes Match subscription ended in October. All the files are DRM-free AAC files. I'm encouraged (that I have DRM free copies) and really bummed out (because iTunes won't serve them up to me on any of my devices by default).

So I'm not sure where exactly to go from here. I may try to hack something together where I edit my iTunes database to update play counts and hopefully get that reflected on my linked iTunes libraries. We'll see how that works out.

I don’t want to end on a negative note, so I will point out that I’m happy to have Apple Music. It’s been a great service an I’ve found new music that I really enjoy as a result of it. I bet that mine is a crazy edge case resulting from the years of my account’s activity. If you’re on the fence about a streaming service, don’t hesitate to give Apple Music’s 3 month trial a go.