Before getting hormones or surgeries, transgender people typically obtain letters from mental health professionals to authorize medical transition. This validation process stems from guidelines issued by the World Professional Association for Transgender Health which is based on the cultural assumption that transgender people have gender dysphoria. When trans people seek therapy to get letters of authorization, the “golden tickets” to medical transition, the negative labeling of mental illness informs this process. Using interviews with 20 trans men—female-to-male transsexual men who had gotten hormones and/or surgery—this study examines how people managed therapy expectations in accessing medical transition. How do trans men handle the stigma of mental illness in their interactions with therapists? How do they respond to therapy expectations that rely on psychological labeling when accessing hormones and surgery? The results show how trans men used three different strategies—submission, manipulation, and resistance—to minimize the stigma of mental illness and maximize their agency in pursuing different bodies. These stigma management strategies highlight the ways trans men reframed their experiences as normal.