Adolescents with Asperger syndrome (AS) are increasingly being placed in academically focused high schools. These students, although academically able, may not be coping with the wider classroom and social demands of transition to, and within, the high school environment. Schools are keen to enroll these students. However, there appears to be a gap between the rhetoric and the reality relating to the varying perceptions of key stakeholders. In this paper we present the results of a study of the perceptions of key stakeholders in the transition of two students with AS into two academically focused high schools. Eight participants were involved in semistructured, one-on-one interviews. Key stakeholders included executive teachers, classroom teachers, students and their caregivers. The results indicated that there were some differences in the teacher and caregiver perspectives across physical, academic and social areas of transition.