Federico Kirschbaum on XBOW, AI Hackers, and the Future of Pen Testing

From Three Buddy Problem by Security Conversations

May 25, 2026 · 58 min

About this episode

Federico Kirschbaum discusses the impact of AI on penetration testing and the future of offensive security.

( Presented by TLPBLACK : A cybersecurity intelligence platform focused on sharing curated, high-sensitivity threat insights and research with trusted security professionals. ) Three Buddy Problem x Ekoparty Miami : Federico Kirschbaum, founder of Ekoparty and now head of Security Lab at XBOW, talks about what happens to offensive security when an autonomous AI hacker can find and exploit real vulnerabilities. Fede walks through XBOW's "Tales from the Trace," the surreal experience of watching a non-human adversary reason its way to an ASLR bypass, and why he believes pen-testing isn't dying but finally becoming accessible to far more than the world's biggest companies. Plus, where humans still matter in the loop, whether an LLM-discovered bug is public by definition, the looming reckoning over software liability, and Halvar Flake's very honest fear of getting lazy. Cast: Juan Andres Guerrero-Saade , Ryan Naraine and Federico Kirschbaum . Timestamps: 0:00 Fede's move to XBOW 2:20 What's XBOW building? An AI hacker for real vulnerabilities 5:53 Where the human stays in the loop 6:35 The Exim bug: a craftsman races the LLM to an ASLR bypass 10:49 Does bug discovery still need a…

People in this episode

Hosts: Juan Andres Guerrero-Saade, Ryan Naraine

Guest: Federico Kirschbaum

Topics covered

cybersecurity
AI hacking
penetration testing
vulnerability exploitation
software liability

Keywords

AI hacker
vulnerabilities
pen-testing
bug discovery
software liability
Ekoparty
XBOW

Mentioned in this episode

Organizations: XBOW, Ekoparty, Security Lab, Metasploit, CORE, Satan