My storage room is filled with boxes of CD jewel cases with all of the music I purchased before the digital revolution. At a certain point, it just became easier to just buy music digitally. In fact, In many cases I repurchased music digitally because I didn’t want to be bothered digging through boxes to find my CD version. Unfortunately, much of that music was purchased on iTunes, and Apple frequently decides to not let me listen to the music I purchased from them.

Let me illustrate by recounting my Tuesday experience.

It was the first snow of the year, so I decided to do some coding in my front room so I could look out the front window and enjoy the view. One last thing to make the moment perfect: Music.

So I open up iTunes and browse through my library until I find a song. I press “play” on the song, only to be greeted by a login dialog. I enter my apple ID and password and it informs me that I have already authorized 5 out of 5 computers for listening to this song. Well, that’s inconvenient. I have no idea which computers I have authorized, so, after some Google searching, it seems I need to deauthorize all of my computers. I log into my apple account and find the button I need to click to deauthorize all my computers, then I start again.

I return to the song that I want to play, and am greeted with a login dialog again. This time, after typing in my password, it informs me that I have authorized 1 out of 5 computers for this song. And then… nothing happens.

So I click the song again. It again pops up with login dialog, so I enter my username and password again. And…. nothing happens.

Rinse and repeat a few times – each time accompanying the login with louder and more creative profanity. Log out of iTunes. Log in….

Still cannot play this song. For the love of God! This was just supposed to be ambiance, and now it has derailed my day.

I go and try to play the song on my other computer where it used to work.. And, of course, it no longer works because of the deauthorization I initiated a few steps before. But I have now authorized the song on two computers – whatever that means – it obviously doesn’t mean I can play the songs.

Then a small breakthrough. I notice that one of the login dialogs is prompting me to sign in with my old university email address (which I amalgamated into my new email address about 8 years ago). When I logged in with that old address, it required me to again authorize it. But that appears to be under a different accounting system than my new address, because it insisted that the song had been authorized on 5 of 5 computers.

So I follow the same deauthorization procedure with my old address and start again.

I go back to the song and try to play it. I fill in the login dialog (with my old email address), and it informs me that I have authorized one out of 5 computers. And then…. it plays!

Yay! Clearly this is some computer glitch in Apple’s system with respect to my email addresses. The old address was supposed to cease existence when I switched it those many years ago. And it appears to be linked in some ways (e.g. It works with the new password that I set on my new address recently — so the password is linked), but my music authorization doesn’t work.

So problem solved right?

Actually, now, for some reason, I need to log in to play every single song I’ve ever purchased from Apple. One might think I just need to login once, and everything would work. But no, I need to login each time I want to play a song. In many cases I need to use my old email address to play the some. In some cases I need to use my new address, and in another bunch of cases, I still can’t play the song at all.

I’ve spent time with Apple support in the past (years ago), and never really found a solution. Since this is just ambiance, I’m reluctant to waste a day going through those steps again.

All I can do is:

1. Never purchase another digital product from Apple again. It’s too risky.
2. Find the CD copy in my storage room, and rip that onto my computer.

One funny thing about this incident, is that when time came to vent to my wife later, it turned out that she had a similar experience that same day where 2 songs had just been “removed” from her library for no apparent reason (songs she had purchased!!). They’re gone. Hmmm