This chapter reflects on children’s rights to education and play by analysing young children’s experiences of their transitions from pre-primary provision to school in Chile. The chapter critiques adherence by the State of Chile to the United Nations Convention on the Rights of the Child (UNCRC) and identifies that recent national policies in Chile have required primary school and early childhood educators to collaborate to promote transition practices that privilege young children’s play. The chapter illustrates how this policy drive has translated into practice by drawing on an empirical study which found that young children’s greatest concern about moving to the first grade was the paucity of opportunities to play, especially outdoors (Jadue-Roa et al., 2016). The authors argue that if young children express their need to play outdoors, their educational provision should accommodate such play, and that it is therefore necessary for teachers in early childhood education and care and primary school education to understand that need and how to accommodate it. The authors claim that this argument is fundamental for securing compliance with young children’s UNCRC rights to play, education, their right to be heard and their best interests.