Uploaded August 2026 | Updated September 2026, 2 weeks ago
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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🔥 EPISODE LINK 🔥
unchainedcrypto.com/dex-in-the-city-how-claudes-red-teaming-agents-escaped-a-test-without-realizing-it
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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 cape.co/unchained (use code: UNCHAINED).
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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.
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Host:
⭐️ Katherine Kirkpatrick Bos, General Counsel, Host of DEX in the City and General Counsel of Chainlink - https://x.com/kkirkbos
⭐️ Jessi Brooks, General Counsel at Ribbit Capital - linkedin.com/in/jessi-brooks-8289ab32
⭐️ Vy Le - Co-host of DEX in the City and General Counsel of Veda - https://x.com/TuongvyLe12
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 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
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#bitcoin #ethereum #crypto #cryptocurrencies
=========================================================================
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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.
=========================================================================
🔥 EPISODE LINK 🔥
unchainedcrypto.com/dex-in-the-city-how-claudes-red-teaming-agents-escaped-a-test-without-realizing-it
=========================================================================
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 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, General Counsel, Host of DEX in the City and General Counsel of Chainlink - https://x.com/kkirkbos
⭐️ Jessi Brooks, General Counsel at Ribbit Capital - linkedin.com/in/jessi-brooks-8289ab32
⭐️ Vy Le - Co-host of DEX in the City and General Counsel of Veda - https://x.com/TuongvyLe12
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 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
=========================================================================
#bitcoin #ethereum #crypto #cryptocurrencies
=========================================================================
Subscribe to our channel!
CHECK OUT THE CRYPTOPIANS → youtube.com/watch?v=DFzunCFXrv4 WEBSITE → unchainedcrypto.com
UNCHAINED DAILY NEWSLETTER → unchainedcrypto.beehiiv.com/subscribe LAURA'S TWITTER → https://x.com/laurashin
UNCHAINED TWITTER → https://x.com/unchained_pod
FACEBOOK → facebook.com/unchainedwithlaurashin
INSTAGRAM → instagram.com/laurashin/?hl=en
LINKEDIN → linkedin.com/in/laurashin
MERCHANDISE → https://unchainedpodcast.company.site/
++++++++++++++++++++++++++++++++++++++++++++++++
NEW EPISODES OF UNCHAINED EVERY TUESDAY AND FRIDAY!
ALONG WITH BITS & BIPS AND THE CHOPPING BLOCK
Apple → podcasts.apple.com/us/podcast/id1123922160?ls=1
Spotify → open.spotify.com/show/1cJrrfGY1SKBIRn5noKSAf?si=6SI4qIcRTEO7EhOe0V9n4w
RSS Feed → https://feeds.megaphone.fm/LSHML4761942757
YOUR NO-HYPE RESOURCE FOR ALL THINGS CRYPTO!
