Background: As part of the residency application process in the United States, many medical specialties now offer applicants the opportunity to send program signals that indicate high interest to a limited number of residency programs. To determine which residency programs to apply to, and which programs to send signals to, applicants need accurate information to determine which programs align with their future training goals. Most applicants use a program's website to review program characteristics and criteria, so describing the current state of residency program websites can inform programs of best practices., Objective: This study aims to characterize information available on obstetrics and gynecology residency program websites and to determine whether there are differences in information available between different types of residency programs., Methods: This was a cross-sectional observational study of all US obstetrics and gynecology residency program website content. The authorship group identified factors that would be useful for residency applicants around program demographics and learner trajectories; application criteria including standardized testing metrics, residency statistics, and benefits; and diversity, equity, and inclusion mission statements and values. Two authors examined all available websites from November 2011 through March 2022. Data analysis consisted of descriptive statistics and one-way ANOVA, with P<.05 considered significant., Results: Among 290 programs, 283 (97.6%) had websites; 238 (82.1%) listed medical schools of current residents; 158 (54.5%) described residency alumni trajectories; 107 (36.9%) included guidance related to the preferred United States Medical Licensing Examination Step 1 scores; 53 (18.3%) included guidance related to the Comprehensive Osteopathic Medical Licensing Examination Level 1 scores; 185 (63.8%) included international applicant guidance; 132 (45.5%) included a program-specific mission statement; 84 (29%) included a diversity, equity, and inclusion statement; and 167 (57.6%) included program-specific media or links to program social media on their websites. University-based programs were more likely to include a variety of information compared to community-based university-affiliated and community-based programs, including medical schools of current residents (113/123, 91.9%, university-based; 85/111, 76.6%, community-based university-affiliated; 40/56, 71.4%, community-based; P<.001); alumni trajectories (90/123, 73.2%, university-based; 51/111, 45.9%, community-based university-affiliated; 17/56, 30.4%, community-based; P<.001); the United States Medical Licensing Examination Step 1 score guidance (58/123, 47.2%, university-based; 36/111, 32.4%, community-based university-affiliated; 13/56, 23.2%, community-based; P=.004); and diversity, equity, and inclusion statements (57/123, 46.3%, university-based; 19/111, 17.1%, community-based university-affiliated; 8/56, 14.3%, community-based; P<.001)., Conclusions: There are opportunities to improve the quantity and quality of data on residency websites. From this work, we propose best practices for what information should be included on residency websites that will enable applicants to make informed decisions., (© Paulina M Devlin, Oluwabukola Akingbola, Jody Stonehocker, James T Fitzgerald, Abigail Ford Winkel, Maya M Hammoud, Helen K Morgan. Originally published in JMIR Medical Education (https://mededu.jmir.org).)