Living labs are increasingly used as an approach for facilitating innovation and testing emerging information technologies. In this paper we analyse three large-scale technology design projects in Danish healthcare where co-design and implementation activities were organised in living labs. We describe some of the critical challenges that we experienced from transitioning technology prototypes and co-design activities into becoming part of the daily lives of patients, citizens and healthcare practitioners. The main challenges relate to creating and sustaining new work practices, scaling the number of participants, and facilitating the transition between everyday life and living lab behaviour.