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Episode 189: The Present and Future of AI-enabled Pentesting

Cybersecurity Where You Are · 2026-05-27 · 34 min

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Episode notes

In episode 189 of Cybersecurity Where You Are, Sean Atkinson sits down with Ed Skoudis , President of SANS Technology Institute. Together, they discuss the present and future of pentesting enabled by artificial intelligence (AI). Here are some highlights from our episode: 00:39 . Introductions to Ed 01:49 . The promise of AI-enabled pentesting in creating more secure infrastructure 04:52 . AI-enabled and AI-centric workflows in the realm of penetration testing 08:03 . Wranglers, matadors, and centaurs, oh my! Metaphors for AI-enabled pentesters 13:00 . How AI can assist with reporting, enumeration, and scanning as part of a pentest 14:57 . AI-enabled source-assisted pentesting and the types of vulnerabilities it finds 19:50 . A learning opportunity for the broader cybersecurity community 23:44 . How AI and human analysts could split the workload in a future penetration test 25:54 . AI-enabled pentesting vs. AI pentester in a box 29:51 . Why "human in the loop" might be too passive a phrase 30:37 .

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