This paper investigates the transition experiences of students with intellectual disability, as they move from primary to secondary school in New South Wales, Australia. Employing a multiple case study approach, the authors investigated the transition from the perspective of the students experiencing it. During the study, ten students with mild to moderate intellectual disability participated in interviews and were observed in the school environment before and after they transitioned from primary school to secondary school. Results indicate that students with intellectual disability generally have a positive transition experience. Nevertheless, students commonly encounter a number of major challenges, including issues around managing school work and homework, and bullying. The study found several factors contribute to a successful transition. These include the provision of assistance to help students become familiar with and manage their physical environment, building positive relationships with teachers, and having extra support from special needs staff. The study suggests there are some simple and practical steps that schools can take to enhance outcomes for successful transition experiences.