Reversal of gender-discriminatory insurance coverage policies has led to a substantial increase in access to gender-affirming surgical care in the United States over the past 20 years. Although the evidence supports the safety, feasibility, and medical necessity of gender-affirming hysterectomy and oophorectomy, there are currently no evidence-based guidelines to define optimal care surrounding many aspects of these surgeries. This commentary reviews the evidence supporting the safety, feasibility, and route of hysterectomy and oophorectomy for transgender men, the benefits and risks of oophorectomy in cisgender women and their extrapolation to transgender men, and the effects of testosterone supplementation in transgender men with and without ovaries. In addition, this article highlights the data gaps surrounding whether oophorectomy should be performed at the time of hysterectomy. Oophorectomy in cisgender women is associated with negative outcomes such as an increase in cardiovascular events and all-cause mortality, most likely attributable to attenuated estrogen levels. There are insufficient outcomes data regarding oophorectomy in transgender men to make the same inference about potential morbidity and mortality. Areas for future research to elucidate best practices are identified in the context of the increasing number of gender-affirming surgeries. As physicians, it is our duty to provide transgender patients with evidence-based recommendations on gynecologic gender-affirming care and to avoid any potential harm.