How AI Agents Could End the UI-Based Annoyance Economy

Opening

Hello, subscriber! Do you remember the newsletter I wrote about Adobe’s dark patterns a while back? Lately, the topic has been heating up in the US as a string of dark-pattern lawsuits reach their verdicts. Have you ever tried to cancel Amazon Prime? You have to click through 4 pages, hit 6 buttons, and navigate 15 separate choices. Amazon employees internally called this cancellation process the “Iliad Flow” — a name borrowed from Homer’s epic poem The Iliad, meaning a journey as long and grueling as the ten-year Trojan War.

And this isn’t unique to Amazon. A report published this past February by Stanford economist Neale Mahoney and Chad Maisel of the Groundwork Collaborative calculated the total cost of this “annoyance.” The figure: $165 billion a year for American households — roughly ₩250 trillion in Korean won. The report called this the ‘Annoyance Economy.’

Reading this report, a different question came to mind. This annoyance only works under one precondition: a human has to sit in front of a screen and click through it themselves. What happens if that precondition disappears?

🔍 Anatomy of a ₩250 Trillion Annoyance

Mahoney and Maisel’s report broke the annoyance economy’s costs down by category: $33 billion (~₩50 trillion) in damage from spam and robocalls, $21.6 billion (~₩33 trillion) in insurance-related administrative overhead, $90 billion (~₩136 trillion) in hidden fees of various kinds, and $19 billion (~₩29 trillion) lost to medical wait times. On average, 130 million spam and illegal marketing calls are placed in the US every day, and 20 billion spam texts go out every month.

But here’s the truly interesting part. Research shows that companies which made cancellation harder saw revenue increase by anywhere from 14% to as much as 200%. That’s the central finding of a 2023 paper¹ by Stanford’s Liran Einav, Benjamin Klopack, and Mahoney. It means that hard-to-cancel processes aren’t a simple mistake or an inertia problem — they’re a deliberately engineered revenue model.

Amazon’s “Iliad Flow” is the textbook example. In September 2025, just three days into its trial against the FTC (the US Federal Trade Commission), Amazon agreed to settle for $2.5 billion (~₩3.8 trillion). Internal emails released during the trial showed employees referring to unwanted subscriptions as an “unspoken cancer” and describing the practice of pushing subscriptions on customers as “a bit of a shady world.”

Annoyance isn’t a bug. It’s a feature.

And the damage doesn’t stop at people’s wallets. According to a 2019 survey, nearly a quarter of respondents said they had delayed or given up on medical care because of administrative hassle. The time spent on scheduling appointments, filing insurance claims, and processing paperwork alone amounts to $21.6 billion a year. The annoyance economy isn’t just draining money and time — it’s eating into our health.