This chapter focuses on medical students' experiences in transforming from face-to-face to distance learners in a Swedish regionalized medical program (RMP). One group of students (n=100) were followed during six semesters through surveys, log data, observations, and in-depth interviews. A research model built on the Cultural-Historical Activity Theory (CHAT), including the notion of dominant and non-dominant activities, was used in order to identify factors that influence students' stepwise transformation from face-to-face to distance learners. The analysis contains the investigation of pedagogical, institutional, and historically grounded conflicts that seem to inhibit medical students from making a complete transformation to distance learners. By going deeper into the analysis of transitional actions, which seems to help in solving conflicts, the chapter discusses implications to facilitating medical students' future transformation from face-to-face to distance learners. These implications are examples of curriculum redesigns, such as new educational designs and integration of technology and pedagogy in the curriculum.