High school students with autism spectrum disorder (ASD) often struggle in the complex social and academic secondary environment. Current literature suggests postsecondary success is limited for adults with ASD, but little is known about the high school experiences of individuals with ASD that may be impacting their postsecondary outcomes. Focus groups with multiple stakeholders were used to examine challenges facing high school students with ASD and their service providers. Through qualitative analysis, three themes emerged that illuminate challenges posed in the high school setting for students with ASD: (1) inconsistencies, many of which are intrinsic to the secondary environment, (2) difficulties with interpersonal connections, and (3) knowledge/process breakdowns. The findings demonstrate the misalignment or “crack” that exists between the nature of high schools and the needs of students with ASD as they prepare for success in postsecondary environments.