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Oral and maxillofacial residency programs remain male-dominated with 80% of residents identifying as male. This study explores the experiences of the first woman oral surgery resident in a college of dentistry to better understand barriers to women’s equitable inclusion within this profession. Three semi-structured interviews were conducted during the participants first year of residency. Data were coded and synthesized into short narrative passages for analysis using Acker’s (1990) Theory of Gendered Organizations. Results indicated that gender prejudice and discrimination might play a role in why women may avoid applying for and enrolling in oral surgery residency programs. Recommendations for how institutions and programs can create more equitable spaces for women are made based on this unique case.