From clinical trials to care delivery, advanced, digitally enabled technologies and analytics offer new approaches to how we think about medicine, health, and biology. The Covid-19 pandemic has accelerated this conversation, and forced a roadmap, once measured in years or decades, to unfold over days, weeks, and months. Yet the scaffolding for this roadmap had already emerged prior to the Covid-19 pandemic. In this perspective, we highlight a special collection of papers on “digital medicine,” which emerged from a symposium held in Boston in 2019 and were published in 2020 and 2021. The symposium was hosted by Harvard Business School and the Harvard MIT Center for Regulatory Science, and included a range of speakers and attendees from industry, government, and academics. We describe their ongoing relevance as we contemplate our early 2021 pandemic reality and the near future of digitally empowered health care.