Living off the land with Spencer Alessi
Aired September 21, 2026 | 46 min
Andrew welcomes back pen tester and AD security enthusiast Spencer Alessi (Tech Spence) fresh off DEF CON for a wide ranging chat on where PowerShell still fits into offensive security, how AI is changing his workflow, and what makes an environment genuinely painful to attack. Spencer talks through why PowerShell remains a favorite for both attackers and defenders, how he uses LLMs to speed up one off scripting tasks (and where they still fall short), and how he leans on AI tools to obfuscate offensive tooling during engagements. The conversation shifts into real world stories from the field, including a memorable case of exposed domain user hashes sitting on an overly permissive share, before wrapping up with the three controls Spencer sees make the biggest difference for defenders: application control, content filtering, and network segmentation.
Meet our guest
Former Sysadmin, now Pentester @SecurIT360 | Microsoft MVP | Helping IT teams make their environment harder to attack | Social Media content & podcast @CyberThreatPOV
Meet our host
Andrew Pla
Andrew Pla, a seasoned IT professional with over 10 years of experience, has spent the last 5 years mastering PowerShell. An ardent member of the PowerShell community and a Microsoft MVP, he loves sharing his knowledge and leveraging automation to solve complex problems. You can always find him connecting with others on the PDQ Discord and troubleshooting, with the firm belief that a problem shared is a problem halved.
