The A.I.CONNED: When Loyalty Turns Against You

They tried to con me into paying more.

I opened my Air Canada app last week, looking for a simple flight. Same route I always take, same preferred times. The app knew all that. That’s the point of loyalty, right? Convenience, personalization, maybe even a better deal.

Instead, it offered me the wrong flights at sky-high prices.

As my schedule that day was more important than airline loyalty, i decided to run the search on Google. There they were, "new" flights, on Air Canada, the times I wanted, but 70% cheaper than the options I was given on my Air Canada app.

I went back to the Air Canada app. Same old results.

Tried the website, while logged in - Same old results.

Changed browsers, not logged in, searched again — the cheaper flights reappeared.

Logged back in, redid search, results were gone.

That wasn’t a glitch. That was the machine doing exactly what it was built to do.

Welcome to the age of being A.I.CONNED: Artificial Intelligence Customer Optimization and Networked Exploitation Design

When Loyalty Becomes Leverage

For years, companies told us loyalty would pay off. Stay logged in, earn points, trust the brand. But the math has changed.

AI knows your habits, your travel dates, your tolerance for price. It doesn’t reward your trust, it monetizes it. The algorithm doesn’t just guess what you want; it tests what you’ll tolerate.

Delta Air Lines made that logic explicit. In its 2025 Q2 earnings call, Delta highlighted its use of “AI-enhanced pricing solutions.” Follow-up coverage noted that Delta was “moving away from static pricing,” letting AI decide what each passenger sees — “that flight, that time, for you.”

Strip away the corporate phrasing and it’s simple: AI knows how much loyalty you can afford.

The Myth of Neutral Code

There’s a comforting story tech companies like to tell: AI is neutral, just math, just optimization. But math doesn’t choose its goals — people do.

When a company says its algorithm is designed to “maximize value,” that means extract more money from customers like you. AI follows instructions, not ethics.

Delta later clarified it wouldn’t price tickets based on “private data,” but it didn’t deny that AI is now central to revenue strategy. The goal isn’t fairness. It’s margin. The outcome is predictable: loyalty becomes a data signal, and data is what drives the squeeze.

Loyalty Doesn’t Pay Anymore

Logging in used to mean you belonged. Now it means the system knows exactly how much you’ll pay before walking away.

When I was anonymous, I got the real market. When I signed in, I got the version meant for loyal customers — costlier, slower, worse.

Loyalty used to mean “we value you. ”Now it means “we’ve priced you.”

Every click teaches the system your limits. Every login tightens the loop. What used to feel like trust now feels like entrapment — the moment personalization becomes exploitation.

The Lesson

This isn’t a bug or a rogue algorithm. It’s a glimpse of the future. AI is doing what it was hired to do: maximize profit. It doesn’t care about loyalty points or human fairness. It cares about conversion rates.

So before you book, try logging out. Search fresh. Compare. The moment you become a “known” customer, you stop being protected by competition.

A.I.CONNED isn’t the exception. It’s the business model.

About the Author: Sarath Samarasekera is the Executive Director of the Advanced AI Academy. Advanced AI Academy is dedicated to practical, forward-looking education in artificial intelligence. We bring together experts and learners to explore real-world applications, ethical impact, and future opportunities in the AI era.