According to Vygotskians, make-believe play, when reaching its mature state, is considered the activity that most contributes to the learning and developmental gains of kindergarten-aged children. Supporting the children in their make-believe play to bring it to a more mature level seems nonetheless challenging for teachers. In this case, teacher’s perspectives are key to gaining a better understanding of the maturity level of children’s make-believe play and the quality of their scaffolding in kindergarten. In this chapter, we document make-believe play in 16 kindergarten classrooms for five-year-olds in Quebec (Canada). The observations conducted using the Mature Play Observation Tool revealed some immature and some mature indicators of make-believe play in the classrooms. Teachers’ perspectives gathered during interviews suggested four possible explanations for the challenges of scaffolding children’s mature make-believe play, enabling us to expand on the observations made in the classrooms: (1) targeting the children’s zone of proximal development, (2) respecting child—initiated and directed play, (3) positioning themselves as a play partner, and (4) intervening with intention within the complexity of their teaching duties. These possible explanations inform the design and implementation of a professional development programme that could support teachers’ praxis regarding children’s make-believe play.