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Engagement with visual art is a promising modality for addressing issues of uncertainty via reflective practice, one that is being increasingly used in health science education. An elective museum-based course for first-year medical students was created by two medical schools and led by an art educator experienced in medical education. The course, Observation and Uncertainty in Art and Medicine, sought to help students explore experiences of uncertainty and to develop reflective capacity through engagement with visual art.The course was run and evaluated from 2014 to 2017, with 47 students participating over the 4 years, with 12 students enrolled per year. Before and after the course, students were given the Groningen Reflection Ability Scale (GRAS) for reflective ability, the Tolerance for Ambiguity scale for ambiguity, and Best Intentions Questionnaire for personal bias awareness, and 35 students (74%) completed all of the scales. Focus group interviews and narrative postcourse evaluations were conducted, coded, and thematically analyzed.Statistically significant improvement was found in GRAS scores. Qualitative themes included student enhancement of observational skills, awareness of the subjectivity and uncertainty of perception, exploration of multiple points of view, and recognition of the course as a place for restoration and connection to classmates.Incorporating visual art into medical education is an effective pedagogical method for addressing competencies central to training, including observation, reflection, and self-care.