Transgender individuals encounter stigma related to nonconforming gender identity, contributing to elevated symptoms of depression, anxiety, and suicidality. Stigma toward transgender individuals (ie, transphobia) poses significant barriers to employment and other areas of functioning. Transgender individuals with a history of mental health concerns may encounter double stigma. The present 2-part study was conducted to investigate experiences of double stigma, internalized stigma, and coping strategies for dealing with transphobia. In Study 1, quantitative findings with 55 transgender participants indicated that employed participants reported higher levels of stigma (both internalized and external). Higher levels of coping with stigma were associated with lower levels of stigma (both internalized and external). Higher levels of coping were reported by participants utilizing psychiatric medication, with lower levels of coping with mental health stigma in particular found among those receiving outpatient mental health services. In Study 2, a grounded theory analysis was conducted with 45 of these participants to identify coping strategies that transgender individuals use to deal with transphobia. Coping strategies were categorized into individual factors (gender normative coping, self-affirmative coping, emotional regulation coping, cognitive reframe coping); interpersonal factors (social-relational coping, preventative-preparative coping, disengagement coping); and systemic factors (resource access coping, spiritual and religious coping, and political empowerment coping). Findings of Study 2 also revealed the presence of disclosure strategies—decisions to reveal or conceal one’s transgender identity, and anticipatory stigma—expecting and preparing for prejudice and discrimination. Results suggest the need for interventions for transgender individuals to enhance coping with stigma and reduce internalized stigma.