I let AI run a penetration test for 30 days. The results were terrifying — but not for the reasons you think.
Let me start with a confession: I was arrogant.
After 15 years in cybersecurity, I’d seen every tool and gadget promise to revolutionize security. They all failed. So when the AI hype train rolled into town, I rolled my eyes. “These algorithms can’t even get my pizza order right,” I’d tell my team. “They’ll never replace human intuition.”
Then my CTO issued a challenge: “Let’s see what happens when you’re not in the driver’s seat.”
For 30 days, I became an AI overseer. My job wasn’t to hack — it was to watch, learn, and occasionally prevent disaster as various AI tools attempted to penetrate our test environment.
What I discovered changed my entire perspective on the future of our profession.
The Setup: Building the Perfect Test Lab
I created a replica of our corporate network — web applications, internal services, even simulated employees with different access levels. Then I assembled the AI “dream team”:
- Reconnaissance: GPT-4 with custom plugins for subdomain enumeration
