Transsexuality remains grounded in pathologizing discourses. Mental health professionals largely classify transgender experiences as disorders, and transgender people seeking to alter their bodies typically must obtain authenticating letters from therapists verifying such diagnoses. Physicians usually require these letters to perform transition-related services, and sometimes require additional legitimization. In these ways, psychomedical professionals impose gatekeeping measures that withhold and confer services to transsexuals who desire medical transition. Using qualitative interview data and grounded theory methods with 20 female-to-male transsexuals, this study demonstrates that transmen typically represent informed consumers whom carefully research psychomedical protocol and anticipate providers’ adherence to professional standards. When they encounter gatekeeping, this preparedness informs their dialectical struggles within the psychomedical institutions wherein transmen must negotiate bodies within the confines of pathology. Ultimately, this dialectical process is managed and maintained by the larger regime of truth—the gender binary system.