Students with autism spectrum disorder (ASD) are attending postsecondary programs at unprecedented rates. Transitions are especially challenging for students with ASD, yet little is known about critical transitions during the college experience. Using the College Adjustment Program Evaluation Scales (CAPES), we examined student and parent perspectives across five dimensions: Student Life, Emotional Adjustment, Independent Living Skills, Interpersonal Relationships, and Self-Advocacy. Sixteen participants—eight students and eight parents, completed the CAPES at the end of fall semester of year one and the end of spring semester year two. Student and parent CAPES ratings were uniformly positive with some differences. We found large effect sizes across dimensions and significant differences in Student Life, Independent Living, and Interpersonal Relationships with parent ratings higher than student ratings. An item analysis revealed specific challenges and skills salient to the results. Implications for supports for students with ASD, higher education practices, and transition research are discussed.