Investigating two longitudinal ethnographic studies of managing gradual adaptation of electronic patient records in Canada and Norway, we conduct a cross-case analysis of the enabling factors that support a continuous transformation of technology and health care practices. In line with previous research, our study shows that large-scale information systems adaptation in health care should be managed by a project-group including not only IT-developers, but also representatives of future users and management. While we also argue for the importance of these meetings, we complement and expand the notion of project meetings by providing a conceptualization of the essential aspects of these meetings. Our conceptualization is composed of continuous reflection-on-practice activities to construct technology-in-use practices. Reflection-on-action activities are internally initiated, and comprise critical reflections by the participants, who continuously evaluate and question work practices in relation to technology.