Researchers increasingly recognize the importance of high school students with disabilities being prepared to advocate for postsecondary academic accommodations. The purpose of this study was to inform how self-advocacy instruction can reflect the authentic context in which postsecondary students with learning disabilities (LD) and with attention deficit-hyperactivity disorder (ADHD) advocate for accommodations. Postsecondary undergraduate students with LD and with ADHD engaged in a video-recorded simulated meeting to discuss accommodations with a standardized (actor-portrayed) professor. A qualitative analysis of the meetings and postsimulation interviews was conducted. Findings demonstrate how students with LD and students with ADHD discuss accommodations with a professor, including their tendency to be hesitant to assert their preferences and needs for accommodations. Data from postsimulation interviews also suggest that participating in and reflecting upon the simulated interview facilitated students to assess their self-advocacy and identify changes they would make in future conversations about accommodations. Implications for research and practice in self-advocacy instruction are discussed.