The move into kindergarten is a critical transition for kindergarten students and their parents as the transition can impact the child’s academics journey through school. It is essential that preschool and elementary schools prepare families for the transition. This action research project studies the question: how can schools make the transition into kindergarten smoother for both incoming kindergarteners and their parents? The researcher reviewed data from the Kindergarten Readiness Assessment of 26 kindergarten students and also conducted a parent survey to determine how schools can better prepare students and parents during the move into kindergarten. The study found the transition practices that focus on building positive relationships between families and schools and increasing communication between preschool and kindergarten educators can lead to successful transitions for kindergarten students and parents.