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As an expression of current challenges faced by contemporary societies, past decades have witnessed heavy demands for higher education to change and transform. One key question here has been the increased digitalization of higher education. Within this wider setting, this thesis deals with an attempt to handle the increasing shortage of physicians in Sweden by way of digitalizing medical education. The aim of this explorative and longitudinal thesis is to describe and analyze structural and educational transformation work in medical education during the digitalization of the program and the transition from face-to-face to distance education. This thesis focuses on teachers, students and management, who are all heavily involved in this transition of the medical program. Two questions guide the research: (1) what are teachers’ and students’ expectations pending the transition, and what are the influences of already established tools and activities on the program and (2) in what ways do conflicts and changes occur over time, and how do teachers, students, and management deal with these as part of the transition? Cultural-historical activity theory (CHAT) serves as the theoretical framework of the thesis. In particular, the concepts of dominant and non-dominant activities, conflicts, transitional actions, and levels of learning inform the analysis. The data are generated by surveys (N = 108), logging of actors’ activity patterns (N = 100 teachers and 100 students), field studies (65 hours), and interviews (N = 62). The data cover teachers’, students’ and management’s roles in the transition. The analysis shows that the way of theoretically understanding the transition – from a dominant face-to-face activity to a new and unproven non-dominant distance activity – have proved to contribute to deeper understanding of the process of digitalizing medical education. The analysis further displays how the transition from face-to-face to distance education creates considerable conflicts that over time force teachers, students and management into structural and educational transformation work. This type of work successively renders new educational design solutions and new flexible ways of organizing distance medical education. This thesis discusses how the structural and educational transformation work forces actors to collectively engage in the transition by experimenting with new suitable methods and designs, as digital technologies and technology-enhanced learning (TEL) could make sense to teachers and students when they are at a distance.