The US Military has made considerable strides in providing quality health care to transgender and gender diverse service members (TSMs). Current policies ensure continued military readiness and allow TSMs to receive gender-affirming care while continuing to serve. Dermatologists play an important role in the multidisciplinary medical team required for medical gender transition; however, there is considerable discord between medically necessary procedures for dermatologic gender-affirming care and insurance-covered benefits. Within the scope of dermatology, many of the available procedures currently are not covered by insurance. This article seeks to discuss how military and civilian dermatologists can contribute to gender-affirming care. We also review existing disparities in health care and identify potential areas of improvement.