Purpose: Along with other industries, healthcare is becoming increasingly digitized. Our study explores how the field of academic medicine is preparing for this digital future. Method: Active strategic plans available in English were collected from faculties of medicine in Canada (n = 14), departments in medical schools (n = 17), academic health science centres (n = 23) and associated research institutes (n = 5). In total, 59 strategic plans were subjected to a practice-oriented form of document analysis, informed by the concept of sociotechnical imaginaries. Results: On the one hand, digital health is discursively treated as a continuation of the academic medicine vision, with expansions of physician competencies and of research institutes contributions. These imaginaries do not necessarily disrupt the field of academic medicine as currently configured. On the other hand, there is a vision of digital health pursuing a robust sociotechnical future with transformative implications for how care is conducted, what forms of knowledge are prioritized, how patients and patienthood will be understood, and how data work will be distributed. This imaginary may destabilize existing distributions of knowledge and power. Conclusions: Looking through the lens of sociotechnical imaginaries, this study illuminates strategic plans as framing desirable futures, directing attention towards specific ways of understanding problems of healthcare, and mobilizing the resources to knit together social and technical systems in ways that bring these visions to fruition. There are bound to be tensions as these sociotechnical imaginaries are translated into material realities. Many of those tensions and their attempted resolutions will have direct implications for the expectations of health professional graduates, the nature of clinical learning environments, and future relationships with patients. Sociology of digital health and science and technology studies can provide useful insights to guide leaders in academic medicine shaping these digital futures.