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AI · May 15, 2025

Chaboo

AI Jailbreaking-- the Game!

Chaboo launched on May 15, 2025 with 9 votes, #2,448 of 7,905 launches that month and more than 50% of that year's launches. The site was still online in September 2026, 1 year on.

What it does

Chaboo is a gamified AI jailbreaking. Daily challenges involve tricking or persuading an AI persona into disclosing secret information, saying something specific, or sending (fictional) money.

A live, buzz-in trivia showdown you run for your friends. You play the host; they fight it out as contestants.

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