This paper examines the conditions under which self-identified trans* men disclose of their transgender identity or past gender history. Drawing upon theories of identity formation, passing and disclosing of stigmatic identities is used to understand when and how disclosure processes happen for trans*men. Drawing on interviews I examine the circumstances surrounding when disclosure or pressure to disclose becomes salient for individuals. I also consider how individuals use and negotiate systems of gender, along other inequalities such as class, race, education, and health care access.