The article describes a comparative case study on children's agentive orientations in two Hong Kong preschools, one is play-based and the other is academically focused. Agentive orientations were measured using Reunamo's interview tool, which focuses on children's uses of accommodative and agentive orientations in everyday situations. The findings show that children in the academically oriented preschool had more uncertain and less participative orientations than those in the play-based preschool. Boys in the academically oriented setting were found to be more vulnerable than both girls and their counterparts in the play-based preschool when confronted with a conflict setting. The results indicate that the play-based environment stimulated children's capacities for agentive and participative social engagement, suggesting that play provides children with the opportunity to develop more versatile social tools and strategies. These competences are of vital importance for successful engagement in collective settings such as classrooms and schools.