A secondary analysis was conducted of the National Longitudinal Transition Study-2 to examine (a) main effects of parents' school and postschool outcome expectations on the actual outcomes achieved, (b) demographic moderators, and (c) adolescent autonomy as a mediator of parent expectations and outcomes. Parent expectations were found to significantly predict study outcomes. Moderator analysis indicated that disability type moderated the relationship between parent expectations and outcomes. Meditational analyses indicated that autonomy did not mediate the relationship between parent expectations and study outcomes. However, parent expectations significantly predicted levels of autonomy, and autonomy predicted a number of postschool outcomes. Together, these findings suggest a need for interventions that support and foster positive parent expectations and parental supports to promote autonomy development. Additional research is needed on the mechanisms by which parent expectations and autonomy affect the outcomes of adolescents with disabilities.