This chapter focuses on medical students’ experiences in transforming from faceto-faceto 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 theCultural-Historical Activity Theory (CHAT), including the notion of dominant andnon-dominant activities, was used in order to identify factors that influence students’stepwise transformation from face-to-face to distance learners. The analysis containsthe investigation of pedagogical, institutional, and historically grounded conflictsthat seem to inhibit medical students from making a complete transformation todistance learners. By going deeper into the analysis of transitional actions, whichseems to help in solving conflicts, the chapter discusses implications to facilitatingmedical students’ future transformation from face-to-face to distance learners.These implications are examples of curriculum redesigns, such as new educationaldesigns and integration of technology and pedagogy in the curriculum.