This mixed-methods study examined perspectives on factors that influence meaningful student and parent involvement in Individualized Education Program (IEP) transition planning. Survey data and open-ended qualitative interviews with urban high school students with a learning disability (LD; n = 16), their parents (n = 9), and their teachers (n = 17) were analyzed. A group comparison of student and teacher ratings on the Student Involvement Survey revealed no difference between students and teachers on level of school efforts to facilitate student and parent involvement. However, qualitative analysis of interview data resulted in the emergence of four primary themes related to challenges to meaningful involvement: (a) facilitation of student involvement in IEP development, (b) challenges to parent involvement in IEP development, (c) challenges and effective supports for graduation, and (d) supports needed for career and college preparation. Recommendations for school practices to support student and parent involvement in the development of authentic IEPs is provided.