This session presents a real-world case study from Air Force Sustainment Command's A4 Logistics division, where AI is modernizing an environment of 60+ applications and 11M+ lines of legacy code processing over a billion transactions annually. We will walk through a four-phase modernization journey applied to the Stock Control System [SCS), combining custom code parsing, graph and vector knowledgebases, and multiple LLMs hosted in USAF Cloud One. The pipeline produces technical and functional baselines, a RAG chat that cites back to source code, an agent-driven COBOL-to-Java refactoring MVP, and a path to a fully modern application. To date, 20M+ lines of code have been extracted and analyzed, with documentation that measurably reduces SME time in technical interchange meetings. Attendees will leave with a reusable blueprint for cutting technical debt and accelerating cloud-native migration across DAF legacy portfolios.