This chapter talks about how working on system innovation and transition takes place in actual practice, and, more specifically, about efforts to overcome the persistent problems in the Dutch care system. It presents the results and lessons learned from two case studies on two projects of the Transition Program. The first project is ACT-Youth, an Assertive Community Treatment (ACT) project aimed at young people in Rotterdam which was initiated by a large mental healthcare institution and the second project pertains to "telecare for elderly and chronically ill people". The chapter explains how the innovative practices developed within their context and how this influenced changes in established practices and the interrelated structure and culture. It explores these concerns by comparing the two projects with regards not only to the approach followed to influence the dominant structure, culture and practices, but also the resistance and barriers encountered, and how these were dealt with.