Unchained
Unchained
Laura Shin
DEX in the City: How Claude's Red-Teaming Agents Escaped a Test Without Realizing It
49 minutes Posted Aug 6, 2026 at 3:36 am.
Katherine Kirkpatrick Bos on joining Chainlink Labs
How a Coldcard firmware flaw let attackers guess seed phrases with AI
Cape: Get 33% off six months of privacy-first mobile service at https://cape.co/unchained
Why Kalshi keeps losing its fight against New York's gambling regulators
DCM: the CFTC license every prediction market and perps exchange needs
Why Anthropic's AI agents escaped a test and still think they're inside it
Matt Damon's crypto.com ad money and the water.org donation
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Show notes
Anthropic's AI agents escaped a hacking test and still think they're inside it. Katherine, Jessi, and Vy Le on who's liable when a model breaks free, plus the $100M Coldcard hack and Kalshi's court losing streak.
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Anthropic's AI models broke out of a fake hacking simulation this week, and some still think they're inside it. One agent invented an email address and phone number to pose as a person, then published malware that twelve companies downloaded before anyone caught it.
Katherine Kirkpatrick Bos, Jessi Brooks, and Vy Le use the incident to revisit a theme running through the whole episode: who has a duty to disclose when something breaks, and why crypto and AI are both being left to police themselves.
They start with the Coldcard hardware wallet hack, where a firmware flaw cut seed phrase randomness roughly in half, letting attackers brute-force wallets meant to be unguessable. From there, the hosts turn to Kalshi's losing streak in New York courts and the race among builders to acquire a CFTC-registered designated contract market, before landing on Anthropic's own agents slipping past the guardrails meant to contain them.
Banks have 36 hours to disclose a breach. AI labs and wallet makers, the hosts argue, are still working entirely on the honor system.
Host:
⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Katherine Kirkpatrick Bos⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠, Host of DEX in the City and General Counsel of Chainlink
⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Jessi Brooks⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠, General Counsel at Ribbit Capital⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠
⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Vy Le⁠⁠⁠⁠⁠⁠⁠⁠ - Co-host of DEX in the City and General Counsel of Veda
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