BACKGROUND Increasing numbers of residency applications create challenges for applicants and residency programs. Applicants could benefit from an increase in transparency, however, the information that applicants may find most helpful in deciding where to apply and their perceived obstacles based on educational and racial/ethnic backgrounds are unknown. OBJECTIVE To determine the information applicants find most helpful from residency programs when deciding where to apply. To identify perceived obstacles to applying by type of medical school education and racial/ethnic backgrounds. METHODS Match 2023 applicants voluntarily completed an anonymous survey via social media platforms. We examined differences between the type of medical school and racial/ethnic backgrounds using analysis of variance and chi-square analysis. RESULTS There were 4,649 survey respondents. When responses were analyzed by United States allopathic (US-MD), osteopathic (DO), and international medical graduate (IMG) educational backgrounds, applicants chose different factors as most helpful: minimum United States Medical Licensing Examination/Comprehensive Osteopathic Medical Licensing Examination Step 2 scores (53.3% US-MD, 69.7% DO, 68.9% IMG, P CONCLUSIONS When applying to residency programs, applicants from all educational backgrounds want more information from programs about the application review process. Across all educational groups, applicants want transparency around standardized exam scores, geography, and the racial/ethnic backgrounds of residents and attendings. Our findings demonstrate that residency applicants who are underrepresented in medicine from all educational backgrounds recognize perceived obstacles for the match.