A sample of 11 male gender-dysphoric patients meeting DSM-III criteria for transsexualism was seen over a 3-year period by a military psychiatrist. Eight patients had extensive military experience, including combat duty in some cases. At the time of evaluation three were on active duty, one was a Department of Defense employee, and four were veterans. Evidence is presented for a hypermasculine phase of development that coincides with the age of enlistment in nearly all cases. The psychodynamic underpinnings of the choice to enlist in transsexual males are discussed. Outcome of military service was premature discharge in over 60%. The military's management of gender-dysphoric servicemen is described. Current military policies, in association with the proposed hypermasculine phase of transsexual development, may actually result in a higher prevalence of transsexualism in the military than in the civilian population.