Electronic medical records (EMR) are now universally used throughout the United States. The rapid and universal use was not due to technical advances by healthcare providers, hospitals, and clinics but by regulation and laws championed by legislative leaders. The electronic health record (EHR) has been cast as the arch villain in many of the narratives about modern medicine ranging from dehumanization to overregulation. Commentators from the worlds of medicine, business, politics, and computer science have all blamed the EMR for many of the issues such as burnout and staff shortages. Artificial intelligence (AI) has also joined in the debate as to its use in medicine. The computer age came for medicine slowly, piecemeal, and with great resistance—until it occurred all at once through several legislative acts. In this chapter, we explore the twists and turns and fits and starts by which medicine tiptoed across a digital chasm that most other industries had long crossed based on research and independent innovation.