Based on a reflection on the tensions between play, education, and learning in early childhood, this article aims to identify and analyze the factors that limit or negatively condition the possibilities for play at school during the transition between early childhood education and primary education in Chile. The study was conducted in four Chilean schools, with the transition levels of Chilean early childhood education (children aged 4 and 5) and the first two levels of primary education (children aged 6 and 7). Based on an ethnographic approach, we combined 22 ethnographic observation days spread over two consecutive years and 59 interviews of various types with children, educators, and parents. The results show structural and material limitations on school play that mainly affect children in primary education. Beyond, factors associated with routines, indications, and statements governing functioning and participation in this level tend to limit or prevent play, often considered a “non-legitimate” activity. Conclusions highlight the potentialities that children’s restricted or resisted play can present in terms of learning.