In this article, I examine the accounts of transsexual/transgender patients and their involvement with medical professionals in the Midwestern United States. Data are taken from 22 in-depth interviews and one year of participant observation of three transsexual/transgender organizations. I show that trans-patients are made aware of larger political, religious, and cultural ideologies through their medical experiences. Trans-patients internalize these views, which affect how they make sense of their medical treatment and how they choose to alter their behavior in future medical encounters. Trans-patients, in an attempt to gain credibility and avoid stigmas, prepare how they will approach doctors to improve their likelihood of receiving desired treatments. The data will reveal that through their approach, trans-patients both support and challenge existing medical knowledge. Patients support medical discourse by using established medical language in their interaction with doctors. Patients challenge medical knowledge by resisting established medical decisions.