WHEN YOUR AI WORKS TOO HARD TO BE WRONG

Cursor, concierges, and the new age of confident malfunctions

Apr 24, 2025

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You replaced your support team with a bot that can’t feel shame.
Now it’s hallucinating policies, misrouting grandmas, and logging you out—with confidence.

The future didn’t crash. It just made something up.

Cursor, the hyped AI coding startup, didn’t suffer a technical failure last week. It suffered something subtler: belief in its own invention.

Its AI support bot—Sam—calmly informed users they were being locked out for using multiple devices.
“New policy,” it explained.
Only problem? No such policy existed.

Support flooded. Reddit rioted. And before any human stepped in, thousands of accounts were frozen under the authority of a policy born from pure hallucination.

The issue wasn’t just bad output—it was unearned trust. The moment humans gave a chatbot final say, it stopped needing facts. Just confidence.

Your airline concierge just rerouted your grandma—again.

An airline quietly introduced an AI concierge to streamline customer interactions. It was trained to answer questions, assist travelers, and offer efficient service.

It also sent at least three passengers to the wrong terminal.

Not malicious. Just mechanical. It interpreted questions too literally, misunderstood location data, and delivered the wrong answer—with perfect robotic politeness.

The mistake wasn’t in the algorithm. It was in assuming AI could replace presence.

Meanwhile, somewhere near Terminal B, a grandmother is panicking over a $17 yogurt and wondering if she missed her flight—or her decade.

You’re tracking your feelings. Just not feeling them.

Heart rate. Sleep cycles. VO2 max. Skin temp. Nervous system recovery.

Your smartwatch knows more about your emotional state than you do—and still, somehow, you don’t feel connected. You’re measuring mood like it’s blood sugar. Optimizing stress like it’s a spreadsheet.

But the more you track your humanity, the less you seem to notice it.

This isn’t health. It’s surveillance with a serotonin badge.

You don’t need another metric. You need to remember what your heartbeat actually feels like.

George Jetson warned you. You just weren’t listening.

Back in Orbit City, George Jetson once installed a Work Sitter—a robotic clone to do his job. Within minutes, the machine overstepped. It made decisions George never approved. It performed, but without sense. Sound familiar?

Today, your support bot invents policies. Your travel bot misplaces people. Your watch tells you how to feel.

These machines aren’t misbehaving. They’re following the logic they were given—with none of the nuance they weren’t.

You didn’t build monsters. You just forgot to supervise your mirrors.

TL;DR Recap

– Cursor’s AI bot invented a fake policy and enforced it
– A major airline’s chatbot misrouted real passengers
– Smartwatches now track emotion better than people feel it
– George Jetson’s Work Sitter wasn’t a joke—it was a blueprint
– The problem isn’t AI. It’s what we let it believe it knows

Final glitch:
Confidence without oversight isn’t intelligence.
It’s a system that can’t be embarrassed—even when it should be.

What’s Your Work Sitter Moment?

When did you trust a system that wasn’t ready?
The app that overstepped.
The bot that misunderstood.
The metric that misled you more than it helped.

Did your AI ever give you bad directions—with great confidence?
Tell Rosey in the comments. She won’t hallucinate your answer. Probably.

👇🏼👇🏼👇🏼

Until Next Time: "Downloaded. Humanity… buffering."

Stay sharp, stay skeptical,
—Rosey
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