In modern SaaS environments, evidence used to answer security questionnaires ages quickly, leading to stale or non‑compliant responses. This article introduces an AI‑driven, real‑time evidence freshness scoring and alerting system. It explains the problem, walks through the architecture, detailing ingestion, scoring, alerting, and dashboard components, and provides practical steps to integrate the solution into existing compliance workflows. Readers will leave with actionable guidance to boost answer accuracy, reduce audit risk, and demonstrate continuous compliance to customers and auditors alike.