Research suggests that students' encounters with professors can be a barrier to students fully accessing disability-related accommodations. This paper describes the use of a clinical simulation as a practice to understand and support how students engage with professors in discussions about disability-related accommodations. The authors detail the use of a simulated meeting with 28 students across two universities, during which they engaged in discussion about accommodations with trained actor-portrayed professors. These simulations were video-recorded and followed by group and individual reflective discussions, which provide students opportunities to review and reflect on their meeting. The authors report the design and implementation of this practice, observations about relational dynamics, and students' evaluations of the authenticity and benefits of the simulation as a learning activity. This simulation approach is recommended as a unique opportunity for practice and reflection that can support students and faculty to work towards meaningful access to accommodations in postsecondary education.