This qualitative study examines, from the perspective of the families, the transition process to employment or postsecondary education for adolescents with learning disabilities (LDs) and the interplay of the roles of parents, students with LDs, and teachers. Using a case study design, series of three in-depth interviews were conducted with five individuals with LDs and with their parents. Data were analyzed inductively. The findings indicate that the families all had informal transition plans; formal transition plans were not written. For four of the families, the transition process was successful and occurred in two phases spanning the elementary and secondary school years. In the first phase parents controlled the transition process, and during the second phase they transferred this responsibility to their children with LDs. Parents' high expectations and advocacy; students' hard work, self-determination and self-advocacy; and teachers' mentoring and support also contributed to the achievement of transition goals. Throughout the process parents, adolescents with LDs, and teachers worked collaboratively. In the fifth case, only the factor of parental advocacy was in place, and it was insufficient to bring about a successful transition for the adolescent with LDs.