Henry Dickson is trapped in a digital hall of mirrors after his iPad crashes and requires a backup restoration. Amazon's security system demands he approve a notification on an app he can't access. Can a loyal customer find a human at Amazon with the power to override a buggy algorithm?

Q: I've been an Amazon customer for more than 20 years. I've spent thousands of dollars on Amazon products, and even contributed to the Amazon Vine program. 

Recently, my iPad was bricked—meaning it was rendered inoperable—during an update. After I rolled it back and reinstalled the Amazon shopping app, I tried to log in. The system asked me to approve a notification sent to the app on that very iPad. Since I was not logged in yet, I could not see or approve the notification. 

Now I'm stuck in an endless loop. Amazon has a recovery link where you can upload a driver’s license to prove your identity, but the link is useless. It requires you to log in before you can upload the documents. If I could log in, I would not need the recovery link. 

I've spoken to a dozen representatives over several days. Some were nice, but most just read scripts and promised to escalate the case. Each escalation resulted in a form email containing the same link that does not work. 

I even tried the account change team at a special phone number. A representative had me email my ID and confirmed he received it. Then I immediately got an automated bounce-back saying the address does not accept incoming emails. 

I've lost access to my Prime benefits and my entire Kindle library. It feels like the company’s tech support is nonexistent and designed to fob customers off. I just want to regain access to the account I have maintained for decades. Can you help? — Henry Dickson, Roswell, N.M.

A: Amazon should have a recovery process that works when you lose access to your primary device, like your iPad. A security system that requires you to be logged in to prove you can't log in is a cruel digital tautology. 

Amazon should also ensure its account change team can actually receive the documents they request instead of pointing you toward a "no-reply" black hole. 

You kept great records of your interaction with Amazon, which was really helpful. But it looks like you also made several increasingly frantic calls to Amazon. When you find yourself in a loop like this, stop calling the main support line. The front-line agents rarely have the authority to bypass two-factor authentication protocols. 

Instead, reach out to an executive. I list Amazon executive contacts on my advocacy site who can actually make things happen. 

I contacted Amazon on your behalf. At the same time, you took a chance and emailed an executive. While Amazon claimed your account was "compromised," it finally disabled the 2FA and the old password. The path back wasn't easy. You hit another wall when the system told you that your cell phone number was already in use. Eventually, Amazon allowed you to re-register your number and regain control. 

"I know your wait has been frustrating and for that, I truly apologize," a representative wrote to you in a follow-up email.

I'm glad you got your account back. You mentioned you're having second thoughts about returning to Amazon after this. That's understandable. If a company makes it this hard to be a happy customer, maybe it’s time to take your business elsewhere—somewhere that doesn’t treat your identity like a math problem it can't solve.

 Christopher Elliott is the founder of Elliott Advocacy (https://elliottadvocacy.org), a nonprofit organization that helps consumers solve their problems. Email him at chris@elliott.org or get help by contacting him at https://elliottadvocacy.org/help/