About
I’m Jesse Kennedy — 20-year Army veteran, retired SFC, offensive security practitioner.
I spent two decades in the infantry. I served as First Sergeant in the 82nd Airborne Division, where I led a company through the withdrawal from Afghanistan in 2021. If you want the full story on that chapter, Scott Mann wrote about the effort in Operation Pineapple Express. You’ll find me in there, but the book isn’t about me. It’s about the people who wouldn’t quit when it mattered most, and the Paratroopers who achieved victory in the midst of hardship and misery.
After the Army I moved into IT and cybersecurity. Not because someone told me to pivot — because I’ve been building, breaking, and reverse engineering systems since before the Army gave me a rifle. I’ve been around Linux since //slackware in 1998. I’m now focused on penetration testing and red team operations, with a particular interest in Active Directory attack paths and AI-augmented offensive security.
What I’m working on:
- Completing the Certified Red Team Operator (CRTO) certification
- Building a fully local AI-assisted pentesting lab (Ollama, Open WebUI, custom tooling on a 4090 rig running Fedora)
- Writing up everything I learn — boxes, methodology, tooling, and the occasional opinion
What I bring:
- Secret clearance
- 20 years of leading people and operations under pressure
- The mindset that if you’re responsible for security, you better know how to break it yourself
This blog is where I document the work. No fluff, no filler. If I post a writeup, I rooted the box. If I post a guide, I built the thing. Everything here is real.