This chapter reviews and discusses Chilean policy development for transitions management in the early childhood education and primary school sector since the educational reform from the 1990s. Firstly, the chapter critically describes how the active political context in Chile has motivated researchers in Chile to explore and understand children’s transition experiences from Early Childhood Education [ECE] to Primary School Education [PSE], identifying the characteristics and influences of playful pedagogies as well as schoolification within the educational system. The second section of the chapter reviews and analyses research in the transition field in the past 15 years, opening the debate about tensions and challenges. The chapter concludes with reflections on future challenges for research and policy, with the aim of supporting better and more respectful transitions experiences in young children’s educational trajectories.