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cross critical infrastructure, we continue to see the same pattern: Organizations invest in OT penetration testing. They receive clean reports. Risks are documented. Leadership signs off. And months later, operations are disrupted by an attack. This isn't negligence. It's a structural problem. Traditional OT penetration testing validates exploits. Modern industrial attacks exploit operations. Those are not the same thing. Most OT programs are optimized to prove controls exist. Attackers are optimized to move undetected across trusted IT–OT paths until impact occurs. In this session, we challenge the model. Terry McCorkle, CEO & Founder of PhishCloud, brings an executive perspective shaped by years of advising boards and industrial leaders navigating IT–OT risk. Chris Weule, Director of Operational Technology, Cyber Fusion & Strategy, brings hands-on adversarial experience modeling how sophisticated attackers pivot across IT and OT environments, exploit trust relationships, and bypass detection before disruption occurs. Together, we explore why *exploit validation does not equal resilience*, why detection, not vulnerability, is the real failure point in most OT incidents. Why accepted risk often becomes operational impact. How to shift from report-driven security to operationally validated readiness. The goal is simple: Move beyond passing tests. Prove your organization can see, stop, and contain a real attack before it affects production, safety, or revenue.