This study explored similarities and differences in the transition expectations of parents and youth. Independent samples of parents (N = 270) of transition-age youth with disabilities and students with disabilities (N = 242) were surveyed about the importance of achieving various adult goals, having specific types of transition-related training and skills, and potential barriers to transition. Factor analysis of the data yielded six scales, and significant differences were found between youth and parents on four of these scales indicating that parents tend to value teacher support more, whereas youth reported higher levels of self-esteem, greater barriers to transition, and more interest in assuming caretaking roles in their future. Parents and students were in agreement, however, around the goals they felt were most important for transition: finishing high school, having health insurance, and having access to a good doctor.