Purpose: To describe the development of the United States Air Force's (USAF) telehealth program from fall 2017 through fall of 2020 in response to the unique challenges associated with providing care for a global transgender military population. Methods: Telehealth visit completion rates were monitored at time of encounters and through electronic health record reports. Patient satisfaction data were obtained by immediate postvisit survey, across provider care received, logistics of setting up the appointment, and quality of the virtual health system connection. Patient cases highlighting opportunities for transgender telehealth were summarized. Results: Between September 9, 2019 and October 28, 2020, 99 telehealth encounters with video-to-video connection occurred. Twenty-three of the encounters were for gender-affirming hormone therapy, 17 for mental health visits, and 59 for speech therapy. Thirty-five surveys were collected from 20 patients. Overall patients were “satisfied” or “very satisfied” with providers' ability to manage their chief complaint through this modality (average 4.9 out of 5 on 1 to 5 scale with 1 being “very dissatisfied” and 5 being “very satisfied”) and “strongly agree” that telehealth is an effective means to accomplish care (average score 4.8 on 1 to 5 scale with 1 being “strongly disagree” and 5 “strongly agree”). Services provided spanned 11 USAF bases worldwide. Conclusions: Telehealth is successful in ensuring ongoing transgender health care services for a global military population. The success of this program may have implications for future military and civilian endeavors to bridge care gaps for transgender patients in resource-poor or distant-site locations.