This study aims to bridge a gap between Vygotsky's seminal framework on the importance of make-believe play and adult scaffolding in children's cognitive development (e.g. executive function [EFs]) and research in cognitive neuroscience. Kindergarten children (N = 160) and teachers (N = 12) took part in the study. EFs skills and make-believe play (Child and Teacher dimensions; e.g. adult' level of scaffolding) were assessed through observation with the "Executive Functions Observation Tool" and the "Mature Play Observation Tool." Results from stepwise polynomial regressions and mediation analysis showed a significant mediating effect of the context on the curvilinear relationship between teacher scaffolding of play and the child's level of EFs. These results show the importance of observing each child and the context in which they learn and play to understand their EFs. Observation of EFs manifestations could allow for better planning of intentional interventions to support the child's skills in accordance with their developmental needs.