Working Theory · № 52

When You Stop Seeing The Gate

25 July 2026 · 1 min read · AI · Systems Thinking · Leadership

I had an interesting moment while building with AI this week.

The agent was searching through a website for information. At one point, it encountered a CAPTCHA.

I expected it to stop and ask for help.

Instead, it simply continued.

Not because it was trying to "hack" anything.

It almost felt like it didn't even recognize the CAPTCHA as a gate. It just treated it as another step in the workflow.

That made me think.

Many systems were designed around assumptions from the old world.

People type.

People click.

People wait.

People solve CAPTCHAs.

But AI interacts with software differently.

It's a bit like designing a city full of gates because everyone walks.

Then one day, everyone starts flying.

The gates are still there.

They're just no longer where the traffic flows.

The interesting part isn't that people suddenly have bad intentions.

It's that the interaction model has changed.

I suspect we'll see more and more examples where defenses, workflows, and approval processes still make perfect sense in the world they were designed for...

but become invisible once the way we interact with computers changes.

When You Stop Seeing The Gate — figure 1
When You Stop Seeing The Gate — figure 2