Youth with disabilities are less likely to enroll and complete postsecondary education than their nondisabled peers. Using a qualitative, cross-case design, we investigated the high school to college transition experiences of young adults diagnosed with Asperger syndrome (AS). Data sources included a family questionnaire, review of special education records, and multiple individual interviews (N = 27) with young adults with AS, family members, teachers, and rehabilitation counselors. Social skills, communication, and executive functioning challenges in high school continued into postsecondary education settings. Across cases, five reoccurring themes seemed to influence the transition from high school to postsecondary education: (a) motivation to attend college, (b) high levels of disability awareness, (c) intentional family supports, (d) coordinated transition planning, and (e) clear postschool goals.