With the onset of the COVID-19 pandemic, the dermatology residency application process rapidly transitioned in a number of dimensions. As in-person activities were canceled and USMLE Step 1 has become pass/fail, there have been several proposed changes to enhance the process, including a push for increased transparency. Given than most dermatology applicants use program websites to learn more about potential residency programs, we conducted a cross-sectional study to quantify how transparent dermatology residency program website were, relative to published guidelines. From February 11, 2022, to February 25, 2022, we examined the available websites of all ACGME-accredited dermatology residencies to determine transparency regarding information dissemination, selection criteria, interview process, program priorities, and program requirements and opportunities. 136 out of 143 dermatology programs (95.1%) were included. Overall, programs were most transparent with program requirements and opportunities (87.25%). This included information on hospital locations, subspecialty clinics, and rotation/call/didactic schedules. Programs were least transparent with sharing their selection and/or exclusion criteria (31.13%) and varied in how much information they shared about the interview process (39.34%), as well as program priorities (64.56%). Opportunities remain for dermatology programs to improve website transparency and aid applicants in this difficult-to-navigate process. These results identify real transparency gaps, with several potential foci for improvement. Our main study limitation is its focus on a single time-period; to ensure that this information remains up to date, ongoing efforts to periodically resurvey content changes is warranted. Our findings provide an overview of programs’ successes and remaining opportunities to follow published transparency guidelines; overall, these findings may guide individual program directors aiming to improve the transparency of their dermatology residency programs and ultimately benefit our future workforce.