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Transition into preschool is a significant milestone in young children’s lives. Previous research on transition consisted primarily of parents’ and teachers’ perspectives which explored and explicated their expectations and concerns during the transition period. This research focused exclusively on preschool principals’ perspectives on the importance of transition and challenges faced during this period. This study adopted a qualitative approach by interviewing three private preschool principals. Findings included detailed descriptions which demonstrated the preschool principals’ perspectives on the importance of transition categorized into four themes which were laying the foundation for learning, managing young children’s behaviors, and understanding routines in preschool. Challenges faced by preschool principals in this study were incompetence of young children, meeting parent’ expectations, separation anxiety, and unqualified preschool teachers. It is hoped that the illustration of the findings contributes to a more holistic knowledge in transition into preschool by aiming to provide a practical solution for preschool principals to overcome these challenges in the future.