Although federal law now mandates age-appropriate transition assessment as a key component of high-quality transition planning, little research exists to guide educators on what they might learn when undertaking this process. In this study, the authors examined teacher and parent assessments of the transition-related strengths and needs of 134 youth with severe intellectual and developmental disabilities who were eligible for the state’s alternate assessment. The perspectives of teachers and parents regarding the transition-related strengths and needs of particular students often diverged in key ways. Students with severe disabilities were perceived as having a range of transition-related strengths across the nine transition domains. Although a number of transition-related needs were identified by teachers, the transition profiles of individual students within this sample were quite heterogeneous. The authors offer recommendations for strengthening the transition assessment and planning process by incorporating multiple perspectives, and present important directions for future research on transition assessment.