It is crucial that future physicians understand the nature of opioid use disorder (OUD). We designed a pilot Observed Structured Clinical Examination (OSCE) using simulated patients (SPs) experiencing OUD with concurrent chronic pain. The case was piloted in 2021 and 2022 during the multi-station OSCE that all the medical school clerkship students take at the end of their third year of medical school. A total of 111 medical students completed the OSCE in 2021 and 93 in 2022. The authors developed a case description and an assessment instrument for the SP to evaluate the student’s performance on history taking, communication and professionalism. The evaluation was mixed-methods using SP evaluation data and a qualitative assessment of medical students’ answers to 4 questions which were analyzed with a priori codes. In both years, the total scores for the case were slightly slower than the established OSCE cases in both years. A total of 75% (148/197) of students who responded to the assessment found the case difficult to manage. Strengths of the case included a majority of the students reporting the case helped them to identify strengths and weakness in assessing and treating OUD. Weaknesses included the lack of enough patient history and the perception that the SP was unrealistic (too nice). This pilot OSCE was challenging for the third year medical students based on the evaluative data. Given the scope of OUD and deaths, training students to identify and treat OUD during undergraduate medical education is of paramount importance.