DORA metrics are the gold standard for measuring software delivery performance and stability. However, conventional methods of capturing these metrics are increasingly challenged by siloed DevOps toolchains, manual data collection, and the growing prevalence of AI-generated code in production. Enterprise delivery pipelines demand resilience and accuracy, but today's measurement systems struggle with both integration complexity and the specialized expertise required to operate in large, distributed environments. This talk will discuss these challenges in detail and show how Generative AI can elevate DORA from static, descriptive dashboards to dynamic diagnostic, prescriptive, and predictive insights—unlocking a new era of actionable intelligence.