Despite advancements in research on sexual morphology as well as increasing interdisciplinary theory on gender, medicine continues to perpetuate anti-transgender stigma in health care. Research on this topic has typically lacked perspectives from health professionals, who operate in and contribute to the environments in which patients seek care. In collaboration with Dallas non-profit Trans Pride Initiative, this study seeks to begin filling this research gap, relying on a sexual stigma framework created by Gregory Herek and applying it to anti-transgender (or gender) stigma to examine its manifestations in health care environments through narrative inquiry. The data from narrative interviews with health care professionals revealed themes of inadequate schooling on transgender competency models and health needs, difficulties in resisting gatekeeper practices while addressing mental health needs, a patient-as-expert approach amongst trans-affirming providers, and understanding of patient family dynamics as a catalyst for understanding stigma. Exploration of sexual identity prior to claiming gender identity, lacking language to explain gender experiences until encountering other LGBTQ+ (lesbian, gay, bisexual, transgender, queer) people, and religious trauma as restrictive to gender exploration during childhood emerged as themes amongst transgender and gender diverse participant interviews. The practical implications of these themes present issues for institutional, social, and legal change due to the pervasiveness of sexual dimorphism (and subsequent gender binary) as a means of structuring medicine, social organization, and legal systems, respectively. Still, critical gender engagement with health professionals pre- and post- licensure has the potential for profound impacts beyond addressing anti-trans stigma in health care.