This event requires an RSVP; to attend, submit form hereTraditional AI assurance approaches-benchmarks, offline testing, over-reliance on human-in-the-loop (HITL), and generic LLM-as-a-judge-fail to capture how systems behave in regulated, real-world workflows. This session examines the gap between model validation and operational oversight, including how institutions handle policy adherence, edge cases, and decision ambiguity. Participants will share how they are designing evaluation layers that reflect real regulatory expectations and human decision standards.