Abstract Background Medical training focuses heavily on clinical skills but lacks in training for navigating challenging clinical scenarios especially with regard to diversity issues. Our objective was to assess third-year medical students’ preparedness to navigate such scenarios. Methods A 24-item survey was administered electronically to third-year medical students describing a range of specific interactions with patients, peers, and “upper-levels” or superiors including residents and attendings, spanning subjects including gender, race/ethnicity, politics, age, sexual orientation/identity, disability, and religion. Students rated their level of comfort via a 5-point Likert scale ranging from 1 (“Very Uncomfortable”) to 5 (“Very Comfortable”). Basic demographics were collected and data were summarized for trends. Results Data were analyzed from 120 students (67% response rate, 54.2% female, 60.8% non-Hispanic white). Students reported lower comfort with peer and superiors compared to patient interactions (p