Many organizations invest heavily in compliance frameworks, policies, and audits, yet still struggle during real assessments or security events. The issue isn’t a lack of understanding—it’s a failure to translate requirements into operational reality. This session examines where GRC programs consistently break down: controls marked “implemented” but not enforced, evidence that doesn’t hold up under scrutiny, and security tooling that isn’t aligned to compliance objectives. Using real-world patterns and examples, we’ll walk through what happens when these gaps are exposed—during audits, incidents, or customer scrutiny—and why traditional approaches fall short. We’ll then shift to what actually works: mapping controls directly to systems and telemetry, generating continuous evidence as a byproduct of operations, and aligning security and compliance into a single execution model. Attendees will leave with practical ways to identify weak points in their own environments and move from static compliance to something that holds up when tested.