Mental health stigma has been identified as a barrier to help-seeking in the United States. This may be particularly salient for military personnel who tend to report higher mental health stigma than the general population. Evidence suggests that both supportive and destructive military leadership are related to service members’ attitudes toward seeking help. In the current study, a sample of military service members and Veterans (N = 232) completed an online survey regarding mental health stigma, previous experiences with military leaders, and mental health help-seeking behaviors. Findings indicated that destructive and supportive leadership experiences were significantly related to self stigma, public stigma, and help-seeking. Military members and Veterans who experienced destructive leadership were more likely to report internalized mental health stigma, which decreased the likelihood of seeking help. Supportive leadership, on the other hand, was associated with greater likelihood of seeking help for mental health concerns, and was indirectly related to help-seeking through lower self-stigma. Findings suggest that the military leadership style plays a significant role in service members’ and Veterans’ willingness to seek assistance for mental health concerns.