This chapter describes the experiences with and lessons from developing and managing a Transition Program in the Dutch care sector (2007–2010). This program encompassed two rounds of 26 transition experiments in actual care practices that were conducted to explore radically new ways of meeting the need for long-term care among the Dutch population. This chapter focuses on how this 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. In addition, we describe initial experiences and lessons regarding scaling up successful transition experiments in healthcare.