🚩 AI moderates itself into oblivion — again  // Romance scammer caught by romance scammer  // Tech CEO discovers what 'trust' means in court  // Platform adds 'good faith' to its terms of service — still undefined  // Dating app launches AI matchmaking for scam detection. Or scamming. Unclear.  // Content moderator wins appeal. Gets their job back. Quits immediately.  // Big Tech executive 'deeply concerned' about the thing his company built  // 🚩 AI moderates itself into oblivion — again  // Romance scammer caught by romance scammer  // Tech CEO discovers what 'trust' means in court  // Platform adds 'good faith' to its terms of service — still undefined  // Dating app launches AI matchmaking for scam detection. Or scamming. Unclear.  // Content moderator wins appeal. Gets their job back. Quits immediately.  // Big Tech executive 'deeply concerned' about the thing his company built  // 
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Flagged Moments

The best/worst/funniest T&S stories of the week. If it made a Slack channel erupt, it belongs here.

1 article
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Flagged Moments

AI Chatbot Designed To Detect Scams Gets Scammed. No One Is Surprised. Everyone Is A Little Delighted.

// The circle of life, T&S edition

A startup's scam-detection AI, deployed to protect elderly users from fraud, received a very convincing email last Thursday about an unclaimed inheritance from a Nigerian prince. The AI, bless its weights and biases, clicked the link.

Feb 15, 2026·4 min read