Beginning with phone calls to an emergency psychiatric hospital and suicide prevention center, the roots of Conversation Analysis (CA) are embedded in systematic analyses of routine problems occurring between ordinary persons facing troubling health challenges, care providers, and the institutions they represent. After more than 50 years of research, CA is now a vibrant and robust mode of scientific investigation that includes close examination of a wide array of medical encounters between patients and their providers. Considerable efforts have been made to overview CA and medicine as a rapidly expanding mode of inquiry and field of research. Across a span of 18 years, we sample from 10 of these efforts to synthesize important priorities and findings emanating from CA investigations of diverse interactional practices and health care institutions. Key topics and issues are raised that provide a unique opportunity to identify and track the development and maturity of CA approaches to medical encounters. Attention is also given to promising new modes of research, and to the potential and challenges of improving medical practices by translating basic and rigorous empirical findings into innovative interventions for medical education. A case is made that increasing reliance on CA research can positively impact training and policies shaping the delivery of humane and quality medical care.