Will AI Replace Human Pentesters?
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Red Teaming in the Age of AI
What does it take to find the vulnerabilities that machines miss? As AI tools become more capable, the question isn’t whether or not they hack (or pentest) – but whether they can think like a human hacker.
In this episode of Threat Talks, host Lieuwe Jan Koning is joined by Melanie Rieback (CEO of Radically Open Security) and Luca Cipriano (Threat Intel Specialist at ON2IT). They explore the uses of AI, the limitations of AI in pentesting, the importance of human intuition and why red teaming remains a craft.
🤖 Can AI outsmart human red teamers?
🧠 What makes great hacking truly human?
🔍 What’s still too complex for automation?
Tune in for a deep dive into the craft of pentesting, the value of experience, and the future of red teaming.
Your cybersecurity experts
Lieuwe Jan Koning
Co-Founder and CTO
ON2IT
Luca Cipriano
Red Team & Cyber Threat Intelligence Program Lead
ON2IT
Melanie Rieback
Co-founder/CEO
Radically Open Security
Episode details
AI vs. Human Pentesting: Who Wins?
What happens when you try to automate something that’s part science, part art? In an industry rushing to adopt AI for everything from detection to response, the real question is: can a machine truly replace the craft of a human pentester?
In this episode of Threat Talks, host Lieuwe Jan Koning is joined by Melanie Rieback, co-founder and CEO of Radically Open Security, and Luca Cipriano, a red teamer and threat intel specialist. Together, they dig into what makes great pentesting work.
Melanie explains why her company donates 90% of profits to open source and operates with a not-for-profit model, and how that connects with their mission to support NGOs and civil society groups. Together, she and Luca share their hands-on experience with pentesting and why creativity, gut instinct, and lateral thinking are still crucial in ethical hacking.
They discuss:
🤖 Can AI outsmart human red teamers?
🧠 What makes great hacking truly human?
🔍 What’s still too complex for automation?
From tool-assisted testing to old-school intuition, this conversation offers a grounded take on the reality of modern pentesting and what AI can’t do (yet).
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