Every career has an origin story, and for longtime CMS leader Lorraine Doo, it begins with the Attachments Rule on her very first day at the agency. In this episode, Lorraine reflects on the evolution of healthcare interoperability—from EDI transactions to APIs, FHIR, and today's digital health ecosystem—sharing behind-the-scenes insights into the policy decisions, collaborations, and regulatory milestones that have shaped modern health IT, along with her perspective on the challenges and opportunities that still lie ahead.