DEX in the City: How Claude's Red-Teaming Agents Escaped a Test Without Realizing It
Unchained | Aug 06 2026 | 00:49:50
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
Timestamps
🩺 02:16 Katherine Kirkpatrick Bos on joining Chainlink Labs
🔐 03:08 How a Coldcard firmware flaw let attackers guess seed phrases with AI
💙 18:32 Cape: Get 33% off six months of privacy-first mobile service at https://cape.co/unchained
⚖️ 19:36 Why Kalshi keeps losing its fight against New York's gambling regulators
🏛️ 30:47 DCM: the CFTC license every prediction market and perps exchange needs
🤖 33:37 Why Anthropic's AI agents escaped a test and still think they're inside it
💧 45:40 Matt Damon's crypto.com ad money and the water.org donation
Learn more about your ad choices. Visit megaphone.fm/adchoices
========================================================
Thank you to our sponsor!
Cape: Your biggest crypto vulnerability isn't your wallet,
it's your phone number. Cape is America's privacy-first mobile carrier
that rotates your SIM identity daily and blocks SIM swaps before they
happen. Get 33% off your first six months at https://cape.co/unchained
(use code: UNCHAINED).
========================================================
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
Timestamps
🩺 02:16 Katherine Kirkpatrick Bos on joining Chainlink Labs
🔐 03:08 How a Coldcard firmware flaw let attackers guess seed phrases with AI
💙 18:32 Cape: Get 33% off six months of privacy-first mobile service at https://cape.co/unchained
⚖️ 19:36 Why Kalshi keeps losing its fight against New York's gambling regulators
🏛️ 30:47 DCM: the CFTC license every prediction market and perps exchange needs
🤖 33:37 Why Anthropic's AI agents escaped a test and still think they're inside it
💧 45:40 Matt Damon's crypto.com ad money and the water.org donation
Learn more about your ad choices. Visit megaphone.fm/adchoices