Medical students are at high risk for developing depression during their training, and programs sometimes fail to make a connection between mental health-wellness events and disability accommodations. When a student presents with chronic or acute mental health concerns, a referral to disability resources may be advisable. In this case, we follow a fourth-year learner with an acute onset of PTSD following a sexual assault. As the team works to address newly developing professionalism issues, the case invites the reader to review disability-related barriers from the perspective of each stakeholder and offers guiding questions for discussing how to integrate accommodations into the system of support for this learner.