Designing for Despair: Don't let your digital interfaces trap members in a doom loop of frustration

What Microsoft Authenticator taught me about bad process design and lasting impressions

I’m currently locked out of my Microsoft account. Not because I forgot my password, or because I triggered a security alert. Nope. I’m locked out because the system designed to help me authenticate… is demanding authentication from itself to do so.

Let me explain.

In order to access my email, I’m required to verify my identity using the Microsoft Authenticator app. But when I open the Authenticator app, it asks me to verify my identity… using the Microsoft Authenticator app!!! No backup. No alternate route. No Face ID, no passcode fallback, no human helpdesk. Just an infinite loop of “please verify using the app you can’t access.”

This is more than just poor UX. It's a failure of process thinking. And this is what people remember.

Not the dashboard. Not the security promise. Not the carefully written welcome email. What I will remember, and what your members will remember, is the moment your system locked them out, left them helpless, and showed no route to recovery. That’s what they’ll associate with your brand.

This is the lasting damage done when digital tools are designed in isolation, without mapping the full experience, and without testing failure scenarios.

This kind of doom loop, where a digital tool asks you to verify something using a method you no longer have access to, is the digital equivalent of shouting into a canyon and hearing your own scream bounce back.

Membership organisations, take note:

• If your self-service portal requires members to guess what email address they used seven years ago and offers no recovery path, they will remember that.

• If your event registration system fails halfway through and wipes their selections, they will remember that.

• If your CPD tracker crashes every time they upload a PDF, they will remember that.

Friction creates memory. And memory builds perception.

When we talk about member engagement, loyalty, or trust, we often focus on value, content, community, and benefits. But nothing undermines all of that faster than a poorly designed digital interface that makes your members feel powerless.

This is not a technical issue. It’s a leadership issue. It’s a culture issue. And it’s a process issue.

Design for the worst-case scenario. Test the escape routes. And never, ever make access to support contingent on the system that’s already failed, because trust isn’t just built on the best day. It’s built on how you handle the worst ones.