Objective Transgender people face unique challenges when accessing health care, including stigma and discrimination. Most residency programs devote little time to this marginalized population. Methods The authors developed a 90-min workshop to enhance residents' ability to empathize with and professionally treat transgender patients. Attendees completed pre-, post, and 90-day follow-up surveys to assess perceived empathy, knowledge, comfort, interview skill, and motivation for future learning. Results Twenty-two residents (64.7 %) completed pre- and post-workshop surveys; 90.9 % of these completed the 90-day follow-up. Compared to baseline, there were statistically significant post-workshop increases in perceived empathy, knowledge, comfort, and motivation for future learning. However on 90-day follow-up, there were no statistically significant differences across any of the five domains, compared to baseline. Conclusions This workshop produced significant short-term increases in resident professionalism toward transgender patients. However, extended follow-up results highlight the limitations of one-time interventions and call for recurrent programming to yield durable improvements.