Although more students with disabilities are attending university than ever before, many still have difficulties with the transition from high school. Transition research has extensively examined the factors and barriers that support or hinder successful transitions for students with disabilities. However, there has been little explicit focus on the "intersection" of experiences with transition and academic accommodations on the overall experience of students with disabilities at university. This study interviewed six participants with various disabilities who transitioned directly from high school to university. Thematic analysis showed that: (a) first-year students are unprepared for the bureaucratic nature of the accommodation process, but ultimately find it fair and non-stigmatizing; (b) first-year students discover that they have to play a more active role in their accommodation planning but ultimately find that this role, and the accommodations they receive, positively supports their autonomy and disability identity at university; and (c) some university instructors exhibit significantly negative attitudes towards students requiring accommodations. These findings have practice implications for disability service professionals in universities supporting the transition needs of students with disabilities.