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This mixed-methods study explores how kindergarteners engage with 21 st century skills during constructive play sessions. Founded in the theories of constructionism, constructivism, and positive technological development, research examines how constructive play with wooden blocks, LEGOs, and Magna-Tiles fosters kindergarteners’ abilities to solve problems, share ideas, and negotiate perspectives. Conducted in a natural classroom setting, the study integrates qualitative observations and interviews with quantitative data to understand how students’ engagement in 21 st century learning supports the inclusion of constructive play in the kindergarten curriculum. The study contributes to current research supporting a realignment of the kindergarten curriculum to include a play-based learning environment that prepares learners to think critically, collaborate effectively, and engage compassionately in a digitally complex world.