The aim of this small-scale, qualitative study is to understand the perspective of varying stakeholders responsible for student transitions from pre-primary to primary school in the Jamaican context. The questions that guided the research are: What factors affect student transitions to primary school? What skills do children need in order to successfully transition? and Who/what is responsible for preparing students to transition from pre-primary to primary school? To answer these questions a representative from the Early Childhood Commission, 13 parents and 16 Grade 1 teachers from 12 schools across the island of Jamaica were interviewed. Findings reveal that student transitions from pre-primary to primary school need systematic attention particularly in light of how this impacts on student success, not only in primary school, but in their secondary years as well. The data also reveal that a major issue affecting student transitions is the quality of pre-primary education and parenting practices in the early years. Also highlighted are the differing perspectives of teachers and parents on the skills needed for success in primary school. Parenting programmes and professional development for both parents and teachers, respectively, are critical if strides are to be made.