The focus of this chapter is on the early preparatory phase of implementation of digital assistive technology (DAT) and the challenges older people, healthcare personnel, healthcare managers and information technology staff may experience. The chapter is based on two independent case studies, both part of longitudinal projects on DAT implementation in municipalities in Sweden and Norway. The two cases provide insights into DAT implementation and its challenges, especially in relation to (1) complex innovation characteristics, (2) external policy and incentives, (3) organisational characteristics and (4) individual characteristics. The authors show how DAT transforms not only work practices and daily routines but also the entire healthcare profession. It changes the emphasis from a primary focus on caring and nursing to a profession involving technological skills. DAT implementation is about transformation and can be disruptive. Thus, successful digitalisation of healthcare needs a new way of thinking, new work practices and new roles and professions.