This article examines the “dilemma of difference” transgender prisoners pose and face within a sex-segregated prison system organized around the pursuit of safety and security. Our analysis uses data from a study of the culture and experiences of transgender prisoners in four men's prisons. Using qualitative data from interviews with transgender prisoners, focus groups with prisoners, and focus groups with staff, our findings reveal a common contention that transgender prisoners are (according to staff) and should be (according to prisoners) treated like everyone else, despite their unique situations. This further demonstrates the stakes that this dilemma carries for the prison regime and transgender prisoners' roles in challenging it without engaging in overt resistance—which carries high stakes for them. Accordingly, we elucidate how the rigidity of an institutional structure built on inherent contradictions can have the potential to complicate the achievement of institutional goals.