In this episode, we dig into whether DAST is dead, mostly dead, or quietly making a comeback dressed in an AI trench coat. The conversation traces the origins of dynamic application security testing from nmap scans and open source hacker tools to a market now valued at nearly four billion dollars and growing. We debate where DAST ends, and AI pen testing begins, whether AI can find a vulnerability nobody has ever seen before, and what happens when you compound the false positives of rigid rule-based scanning with the hallucinations of a large language model. Also: cats meowing the Final Countdown.

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If AI pen testing can already find zero days in open source software, does human pen testing still have a defensible edge — or are we just not ready to admit it doesn't?

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In this episode, we dig into how the cybersecurity personality has shifted from the ego-driven, hoodie-up archetype to the paycheck-chasing newcomer. The conversation covers hype cycles from mainframes to AI to quantum, whether passion or profit is driving the next generation into the field, and why we think the threat modeling problem is already solved. At the same time, everyone else keeps getting in the way. The discussion takes detours through The Cuckoo's Egg, Sneakers, War Games, and NFT apes before landing on a question we couldn't quite agree on: Does AI actually have a personality, and does it belong in the security community?

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If you got into cybersecurity for the love of the problem or the paycheck, would you even know the difference anymore?

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In this episode, we explore what happens when AI agents meet the security principle of least privilege. As agents gain the ability to request permissions, make decisions, and interact with systems on our behalf, the line between human and machine responsibility starts to blur. The discussion covers prompt fatigue, over-permissioned agents, and why "because the agent told me to" may become the next security anti-pattern—before taking a hilarious detour into EULAs, cookie notices, and Matt's unexpected habit of reading both.

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If your AI agent requested administrator access right now, would you know whether it actually needed it?

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