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This Microsoft help page comes with a warning: 'this process requires patience'

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How could something so simple become so hopelessly complicated?

I may have accidentally stumbled into the purgatory of Microsoft online services. It all happened innocently enough: if you're anything like me, you probably set up your Xbox Live account many years ago. Maybe you were even a child or a teenager. And when you were forced to tie your Gamertag to an email address, you probably didn't give it a second thought.

The Hotmail email address I chose that fateful day nearly a decade ago has since become a relic of another time, utterly swamped with spam emails and hindered by an embarrassing account name. It's with good reason, then, that I hoped to switch my Gamertag over to my primary Microsoft account, the email address that now ties together everything from my email and calendar to Microsoft Office and OneDrive. And since Windows 8 is intimately connected to my Microsoft account, the only way I could use the Xbox app on my laptop was if I could decouple my Gamertag from my ancient email address. Little did I know that you're in for a world of hurt if you dare to pair your Xbox Live Gamertag with a different email address.

Pairing your Gamertag to a new email address is a herculean task

The Microsoft support article lists an incredible array of requirements and stipulations if you wish to take on this task. Firstly, there's no way to do from your computer — you'll have to dust off your old Xbox 360 (hope you didn't throw it out!) to accomplish the deed. An Xbox One will not help you. And you better hope that neither your current nor your new Microsoft accounts have any active subscriptions other than Xbox Live Gold or Xbox Music. Otherwise you're out of luck. In addition, the account you wish to transfer to can have none of the below attached to it:

  • An Xbox Live profile
  • A gamertag
  • A billing account
  • An Office 365 subscription
  • OneDrive paid storage
  • Any past purchases from the Windows Store
  • Any other non-Xbox subscription

Oh, and I almost forgot. Any funds tied to your Gamertag will be lost during the transfer.

So I took a deep breath and dove in. I bought a bunch of Mass Effect 3 DLC to burn through the cash left on my account, and went through the process of initiating the Gamertag transfer on my old Xbox 360. After punching in passwords and waiting, a notice appeared: Error 80154013: "This Microsoft account already has an Xbox membership."

Somehow, my new email address had been tied to a generic Xbox Live Gamertag, Player067106467. I kid you not.

Now, this would be funny if it didn't throw a wrench into the entire operation. The error code led me to another Microsoft support article. And whoever wrote it knew that he was about to put people through some 21st century misery. The article warns: "This process requires patience."

Microsoft Xbox 360 avatars

I'm pretty sure no one at Microsoft could be bothered to design a way for people to switch accounts, because the process described is truly dreadful. Since there's no way to delete a Gamertag from a Microsoft account, I first had to make an entirely new, bogus email address. I'd then have to transfer the Player067106467 Gamertag to that bogus email address — a process that first requires me to set up that blank Xbox profile on my Xbox 360. Once the blank Gamertag was removed from the email address I cared about, I could then try to transfer my real Gamertag.

As you can probably guess, this required lots of patience, especially as I typed in long passwords and email addresses with that crummy Xbox 360 d-pad. After I jumped through all the hoops, a message appeared:

"Sorry, we can't change your Microsoft account right now."

Exasperated, I tossed in the towel. Microsoft: 1. Dante: 0.

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