Structural competency is increasingly valued as a framework to address health equity within undergraduate medical education. As of academic year 2023-2024, the Liaison Committee on Medical Education (LCME) requires that medical schools have content regarding basic principles of structurally competent health care. Despite encouraging data about the effectiveness of structural competency curricula, most occur within the walls of a classroom and do not enter the authentic or simulated clinical space. From 2022 to 2023, an objective structured clinical exam (OSCE) focused on premature discharge, previously known as discharge against medical advice, was integrated into the required fourth-year Health Policy course at Weill Cornell Medical College, which uses the framework of structural competency. After a simulated clinical encounter, students completed a reflection assignment and participated in group debriefing to reflect on how policy coursework affected their simulated clinical experience. Students completed an evaluation about their OSCE experience, and OSCE checklist performance was analyzed. Of 82 students who participated in the curriculum, 68 completed a curricular evaluation, and 62 consented to have their OSCE performance evaluated for research. Mean overall OSCE checklist performance evaluating students' patient-centered communication skills, harm reduction skills, and discharge planning and counseling was 14.3/16 (89.6%; standard deviation, 9.8%). Students reported it was valuable to focus on structural factors affecting care within the simulated clinical encounter by using the structural competency framework. To the authors' knowledge, this is the first OSCE for medical students designed to deepen their understanding of structural competency by embedding the experience into an existing course using the framework. Future work should explore how this curriculum affects students' attitudes toward structurally vulnerable patients. With structural competency as an LCME requirement, the use of OSCEs may give educators a means to teach and assess fundamental concepts.