The surprisingly difficult art of paying for my Apple developer account

There comes a moment in every person’s life when they realize that the modern world operates on a system of dependencies so complex that even the companies who built them haven’t the faintest idea how they work. For me, this moment arrived last week when I tried to do something as simple as giving Apple money.

Not just any money, mind you, but money for renewing my company’s developer subscription. The sort of transaction that, in a rational universe, would involve handing over money and receiving goods or services in return. But apparently we do not live in a rational universe. We live in a universe where Apple has constructed a digital Rube Goldberg machine of such staggering complexity that it requires the precise alignment of no fewer than three separate login states, one payment card, one specific biometric authentication method, and what I can only assume is a favorable lunar phase.

“Hello! This is Apple Developer Support,” chirped the first representative with the sort of bright, helpful tone that suggests she genuinely believed this would be a straightforward conversation “How can I help you?”

“I’d like to renew my companys developer subscription,” I said, foolishly believing this was a reasonable request.

“Are you the Account Owner?” she asked, as if I might have called to renew someone else’s subscription for the sheer sport of it.

“Yes. It was transferred to me half a year ago.”

“Great! Are you logged in with your Account in Settings on your Mac, in the App Store, and in the developer App?”

“Well,” I admitted, “I’m logged in with my personal account on my computer and not the business account I want to renew.”

“Sure! Let’s just transfer the ownership to your personal account instead!”

For a brief, shining moment, I thought I had encountered that rarest of creatures: an Apple support representative who understood that technology should serve humans, not the other way around.

“Wait!” she said, and I could practically hear her consulting some sacred text of digital bureaucracy. “I see your personal account is an owner of another organization. I’m sorry, but an Apple ID can’t be an owner of multiple Business Accounts. You’ll then have to log out of Settings, App store, the developer app on your Mac, wipe your iCloud on your computer and then log in again with your business account everywhere.”

There it was, the moment when I realized that Apple, a company worth more than the GDP of most nations, had constructed a system where the simple act of renewing a developer license when you are the owner of multiple business accounts essentially contaminated your entire digital existence, requiring a full cleansing to proceed.

I spent the next hour performing what can only be described as technological exorcism, logging out of everything, wiping iCloud on my computer, and logging back in with my business Apple ID account.

“It’s done,” I reported back, “but I still get the same error.”

Twenty minutes of mystical troubleshooting later, during which we presumably consulted ancient scrolls and performed the technological equivalent of reading tea leaves, my support representative achieved enlightenment: “You know what: I think this will automatically renew in two weeks and you don’t have to do anything.”

Ah. The classic solution: maybe the problem will disappear if we all pretend it never existed.

“Ok! Sure! Thanks!” I said, because what else do you say when someone tells you that the solution to your problem is to have never had the problem in the first place?

Four hours later, my phone rang.

“Hello! This is Apple Developer support! I’m sorry, but what my colleague told you was wrong. Could you log out everywhere on your computer again and wipe your iCloud so that we can renew your developer license?”

At this point, I was beginning to understand that Apple’s support system operates on the same principle as a wobbly table: each attempt to fix the leg makes it wobble more while convincing you that surely, surely, this next adjustment will be the one that works.

“Why,” I asked with what I felt was admirable restraint, “are you making it so hard for me to give you money? Why?” The support representative, to her credit, did not attempt to answer these questions, perhaps recognizing them as the existential screams they were meant to be.

In desperation, I dug up an old iPhone from the technological graveyard that is my kitchen drawer, wiped it clean (because apparently, in Apple’s universe, all devices are born in sin and must be purified), and installed it with my business Apple account.

Surely this would work.

Surely.

It did not work.

Ten minutes into my next call with developer support (call number four, but who’s counting) we finally discovered the solution. To successfully renew an Apple Developer subscription of an organization that was transferred to you (and you use another Apple account day to day), one must not only be logged into the correct account across three seperate applications on a clean device and possess a working payment method, but also have Face ID enabled. Apple, masters of cramming supercomputers into pocket-sized devices, has created a payment system for developers that would baffle the engineers who built those very devices.

And we accept it since we don’t actually have a choice. I couldn’t simply take my business elsewhere, because leaving Apple’s ecosystem would mean abandoning years of work and watching our app vanish from the only store that matters. They can make the process as maddeningly convoluted as they like because what are we going to do? Switch to Android and leave our iOS customer base hanging?

I got my subscription renewed, eventually. But I can’t shake the feeling that somewhere in Cupertino, there’s a room full of very smart people who have created a system so convoluted that they themselves need technical support to use it, and they are just as trapped by it as the rest of us.