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Introduction: The ethical skills fundamental to medical practice encompass a large portion of the Accreditation Council for Graduate Medical Education (ACGME) professionalism milestones. Yet many ethical practices are difficult to reduce to milestone frameworks given the variety of traditions of moral reasoning that clinician-trainees and their colleagues might properly employ. Methods: We developed an observed standardized clinical examination (OSCE) simulation with standardized patients to assess the ethical skills captured in professionalism milestones in pediatrics. The OSCE included four vignettes based on actual cases that presented problems without a correct answer. Residents discussed ethically challenging issues with standardized patients and were evaluated on specific ethical tenets contained in the professionalism milestones. Our assessment guide for preceptors offered content for debriefing and assessment. We piloted this OSCE with seven preceptors and 17 pediatric residents in two different medical settings. Results: Residents all agreed that the four cases were realistic. All but two residents agreed that OSCEs like this one are an appropriate or objective way of assessing the ACGME professionalism milestones. All preceptors reported that they strongly agreed the assessment improved their ability to assess the professionalism milestones. Discussion: This OSCE offers a structured method to assess professionalism milestones and a forum to discuss ethical problem solving. It can also be used solely as a training exercise in ethical decision making and having difficult conversations.