This session at KB4-CON 2026 presents how Intruder combines deterministic vulnerability scanning with artificial intelligence to add contextual investigative reasoning to vulnerability findings and to scale penetration testing expertise. Chris Wallis of Intruder, chief executive officer and co-founder, joins Scott Hebner of theCUBE Research to discuss exposure management, attack surface discovery and agentic workflows for the modern digital workplace. Wallis describes how AI validates and reprioritizes scan results to reduce false positives and to surface higher-risk exposures and they explain Intruder's approach to AI-enabled issue-oriented pen testing that applies expert reasoning at scale while agents run from Intruder's infrastructure. Analysts suggest AI augments pen testing and helps democratize testing for mid-market organizations while closing the gap between high-frequency vulnerability scanning and traditional manual testing. The discussion offers practical perspectives on risk management, cloud security and cyber resilience to inform security leaders evaluating exposure management and attack surface discovery solutions.