Children experience demanding changes during the transition from early childhood programs to primary school. Research shows that children's initial academic and social success at school can affect their long-term adjustment, achievement, and success. The authors, both early childhood teachers in Singapore, undertook an action research project that involved using young children's constructions and pretend play to adapt a transition-related challenge into an authentic learning experience for a group of fourteen 5- to 6-year-olds in a suburban kindergarten. The teachers employed the action research cycle of data gathering and reflection about teaching practice and learner needs, planning and implementation of change to address the problem, and additional data gathering and reflection to assess the effects of the change and to determine future modifications. The teachers concluded that the activities achieved successful cognitive and affective outcomes in supporting the children's ability to apply what they had learned to solve a real-life problem outside the classroom. The children's positive experience contributed to helping them develop positive attitudes about school prior to transition. It also contributed to reducing one potential cause of anxiety and stress for the children and their parents. (Contains 16 figures.)