This chapter describes the experiences with and lessons from developing and managing a Transition Program in the Dutch care sector. It focuses on how the portfolio of transition experiments was developed and managed, including how they were selected, how room was created to set up the selected experiments, how learning was facilitated and how the experiments were monitored. The chapter describes initial experiences and lessons regarding scaling up successful transition experiments in healthcare. It discusses the Transition Program in Long-term Care (TPLC) chronologically. From the onset, the TPLC employed transition management (TM) as its central approach. The chapter describes the background and introduces the program. It includes a detailed empirical analysis of the first three phases of the Transition Program, describing its initial development (phase I), the first round of transition experiments (phase II) and the selection of the second round of experiments (phase III).