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Background: The limited available data suggest that the Canadian surgical workforce does not reflect the racial diversity of the patient population it serves, despite the well-established benefits of patient-provider race concordance. There have been no studies to date that characterize the systemic and individual challenges faced by Black medical students in matching to and successfully finishing training in a surgical specialty within a Canadian context that can explain this underrepresentation., Study Design: Using critical qualitative inquiry and purposive sampling to ensure sex, geographical, and student or trainee year heterogeneity, we recruited self-identifying Black medical students and surgical residents across Canada. Online in-depth semistructured interviews were conducted and transcribed verbatim. Transcripts were analyzed through an inductive reflexive narrative thematic process by 4 analysts., Results: Twenty-seven participants including 18 medical students and 9 residents, were interviewed. The results showed 3 major themes that characterized their experiences: journey to and through medicine, perceptions of the surgical culture, and recommendations to improve the student experience. Medical students identified lack of mentorship and representation as well as experiences with racism as the main barriers to pursuing surgical training. Surgical trainees cited systemic racism, lack of representation, and insufficient safe spaces as the key deterrents to program completion. The intersection with sex exponentially increased these identified barriers., Conclusions: Except for a few surgical programs, medical schools across Canada do not offer a safe space for Black students and trainees to access and complete surgical training. An urgent change is needed to provide diverse mentorship that is transparent, acknowledges the real challenges related to systemic racism and biases, and is inclusive of different racial and ethnic backgrounds., (Copyright © 2024 by the American College of Surgeons. Published by Wolters Kluwer Health, Inc. All rights reserved.)