The State of Pen Testing in 2025 & the Role of AI & Autonomous Solutions (with John Strand)

Today we’re talking about one of the biggest shifts in offensive security that MSPs, CISOs, and defenders cannot ignore.

For years, pen testing was about human creativity — sneaking in where we “shouldn’t” be, showing you how you’d really get burned in an incident. But in 2025, that world is colliding with AI and automated attack platforms that claim they can do it faster, cheaper, and nonstop.

So the question is: are we entering a golden age of continuous validation — or are we fooling ourselves with marketing and dashboards?

To dig into that, we’ve got one of the most trusted names in offensive security: John Strand, Founder of Black Hills Information Security.