We often think of the great capabilities of Generative AI, yet practical, code-first use cases in existing applications remain confined. This session bridges that gap by unveiling a tool that I wrote to streamline .NET application monitoring and WinDbg/SOS-level dump diagnosis through AI orchestration. You will see how to leverage both the advanced reasoning and generative capabilities of LLMs, using them first to fully automate memory dump analysis and generate a report. This approach offers multiple advantages, including removing the reliance on a debugging expert, delivering instant results, and addressing critical privacy concerns. By ensuring sensitive production data is analyzed without human exposure, the process remains fully GDPR compliant. Hardcore debugging has never been this accessible.