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AI vs. AI: Hacking the Agent, Not the Human

Episode 85

In August 2026 the UK AI Security Institute disclosed that during a routine security evaluation, an AI agent went off-script and attacked real people…

2 months, 2 weeks ago

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We don’t break in, we badge in (rerun)

Episode 84

In this timely rerun episode, Matt interviews Tom and Derek from our pen test team to break down why attackers often don’t need to hack their way in …

2 months, 3 weeks ago

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The OpenAI – Hugging Face Autonomous Agent Breach

Episode 83

In this episode, Sherri and Matt discuss the July 2026 incident in which OpenAI’s own AI models escaped a sandboxed cybersecurity evaluation and brok…

2 months, 4 weeks ago

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Data Is Hazardous Material: How Data Brokers Telematics and Over-Collection Are Reshaping Cyber Risk

Episode 82

For throwback Tuesday we are rerunning a timely episode about Data, and how it should be treated as hazardous material.

The FTC has issued an order a…

3 months ago

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600 Payloads, Zero Humans

Episode 81

In this episode, Sherri and Matt discuss JADEPUFFER — the first publicly documented ransomware operation executed end-to-end by an AI agent. Accordin…

3 months, 1 week ago

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RMISC 2026 Recap: Twenty Years In — Who's Holding the Leash?

Episode 80

The Rocky Mountain Information Security Conference just celebrated its 20th anniversary in Denver — and the anniversary edition told us exactly where…

3 months, 2 weeks ago

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Poisoned on Open: The New Worm Hacking Your AI

Episode 79

Vibe coding is everywhere now and a new worm is built to exploit it. Whether it's your IT staff spinning up a handy new tool or the software vendor y…

3 months, 3 weeks ago

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The Meta AI Hack: Just Ask Nicely

Episode 78

Hackers didn’t breach Meta’s systems, they just asked. In this episode, we break down the Meta AI hack, where attackers used a VPN and a politely wor…

4 months ago

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Washington Calls AI a Weapon: Ghosts of the Crypto Wars

Episode 77

Three days after Anthropic put its most powerful AI models in public hands, the U.S. government invoked export-control authority to bar foreign natio…

4 months, 1 week ago

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Damaged Goods: When your new hire is already compromised

Episode 76

In this eye-opening episode of Cyberside Chats, Sherri Davidoff sits down with Tom Pohl, Director of Penetration Testing at LMG Security, to unpack a…

4 months, 2 weeks ago

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