Setting the Scene
Let me tell you a story I never thought I'd write. As someone who's been in the pentesting world for years, developing courses and certifications like CAPIE, I thought I'd seen it all. But then along came a team from Shinobi.Security, led by a guy you might know on social media as Deathspirate. They asked if they could take on my CAPIE exam---the one I'd painstakingly built to be a real challenge, especially for AI.
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I designed this exam with a clear purpose: to push boundaries. It was never meant to be a cakewalk. I loaded it up with business logic flaws, broken access control issues, IDOR vulnerabilities, and tricky corner cases. These were the kinds of nuanced problems I thought would stump even the cleverest AI systems.
And honestly? I was a little cocky. I figured this would be the moment where I could confidently say, "See? Machines still can't beat human creativity."
The Unexpected Outcome
Well, to my surprise and delight, the AI absolutely aced it. It came in, tore through those challenges, and handled them like it was a warm-up exercise. Vulnerabilities I thought would trip it up? Solved. Weird edge cases I had personally struggled with? Checked off the list.
I have to give huge credit to the Shinobi.Security team. Their agentic AI didn't just scrape by---it dominated. And honestly, I loved every second of it. It was humbling, but it was also exciting. It reminded me of something fundamental: as much as we think we know, there's always more to learn. Sometimes the machines really can surprise us in the best ways.
The Lesson Behind the Loss
So here's the thing: not only did the AI beat me that day, but it also taught me something pretty profound. In another exam---(a story for another blog post)---this AI actually gave me a real run for my money and rooted one of my servers. That's not just impressive; that's groundbreaking.
At first, it stung. Nobody likes being outshone on their own turf, especially not on an exam they personally designed. But then I realized: this is the future knocking at the door.
The way I see it, human pentesters aren't being replaced. Instead, we're about to enter a future where AI becomes our teammate. These agentic AI pentesting systems aren't just tools. They're learners, challengers, and partners. They push us to get sharper, think differently, and approach problems from angles we never considered.
A New Era of Collaboration
I've started to imagine what the next 5--10 years of pentesting might look like:
- AI scouts rapidly enumerate targets, mapping entire attack surfaces in seconds.
- Human experts focus on the creative chaining of vulnerabilities, blending context and intuition with AI output.
- Agentic systems keep learning from every engagement, turning pentests into evolving feedback loops of skill-sharing.
- And perhaps most exciting: AI catching the subtle flaws---things like misconfigurations or overlooked logic---that humans sometimes dismiss.
It won't be "man versus machine." It'll be man with machine, against insecure systems. And the organizations we protect will be safer for it.
Final Thoughts
Losing to an AI on my own CAPIE exam wasn't a defeat. It was a wake-up call It showed me that pentesting is evolving faster than any of us imagined---and that's a good thing. It means we're not stuck. We're moving forward.
And honestly? I can't wait to see where this goes. The next time I sit across from an AI in a pentest, I won't see it as competition. I'll see it as a partner, a sparring buddy, and maybe even a mentor in its own strange way.
The future isn't about choosing between human intuition and machine precision. It's about combining them---and setting a whole new precedent for what's possible in cybersecurity.
So here's to the AI agentic pentesters, the human hackers, and the wild frontier where we'll meet. Game on.