In today’s fast‑moving regulatory landscape, static compliance documents quickly become outdated, causing security questionnaires to contain stale or contradictory answers. This article introduces a novel self‑healing questionnaire engine that continuously monitors policy drift in real time, automatically updates evidence, and leverages generative AI to produce accurate, audit‑ready responses. Readers will learn the architectural building blocks, implementation roadmap, and measurable business benefits of adopting this next‑generation compliance automation approach.