This chapter focuses on the early preparatory phase of the digital assistive technology (DAT) implementation process, and explores the challenges older people, healthcare personnel, healthcare managers, and IT-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, in relation to four different categories: 1) complex innovation characteristics, 2) external policy and incentives, 3) organizational characteristics, and 4) individual characteristics. The chapter demonstrates that DAT does not only transform work practices and daily routines but also the entire healthcare profession, from being primarily concerned with caring and nursing to a profession involving technological skills. DAT implementation is about transformation, and may even be disruptive. Successful digitalization of healthcare needs a new mindset, new work practices, as well as new roles and professions.