Dan O'Sullivan revisits a classic Ryanair checkout from about eight years ago, exposing a gauntlet of dark UX tricks that still haunt budget travelers in summer 2026. He maps 9 stages mandatory steps designed to slip extra fees onto passengers, from pre‑checked travel‑insurance boxes to opaque seat‑selection prompts. The post underscores how the airline’s profit model leans on deceptive design for modern travelers today worldwide.

Among the most insidious screens is a ‘Don’t Insure Me’ option buried midway through a country list, forcing users to actively opt out of coverage. Later, a random‑seat lottery appears without a clear ‘no thanks’ button, and a final bag‑fee warning threatens gate‑price penalties. O'Sullivan notes that checking in at the last minute often lands a better seat, a quirk few airlines share.

The walkthrough doubles as a cautionary guide for developers: every added upsell layer compounds friction and erodes trust. Ryanair’s approach shows how profit‑driven UI can survive without regulatory pushback, prompting designers to audit checkout flows for hidden opt‑outs. O'Sullivan’s final verdict: the airline’s relentless upsell engine remains a textbook case of user‑experience abuse and should be studied widely.