While much is known regarding important outcomes of Family-Supportive Supervisor Behaviors (FSSB), little research exists regarding possible antecedents. The present study applies a gender lens to establishing antecedents of FSSB using Social Role Theory (Eagly & Karau, 2002) and Social Identity Theory (Tajfel, 1970). FSSB is a gendered behavior occurring in gendered, ambiguous organizational contexts enabling gender biases to affect supervisor behavior. Thus, I argue FSSB should be predicted from gender variables (gender role attitudes of the supervisor, gender match in the supervisory dyad, and subordinate’s occupational gender type) in the supervisory relationship. An electronic survey was administered to an adult sample of full-time U.S. workers (n =103 matched supervisors and subordinates) in a variety of occupations. Path analysis was employed as the method to test hypotheses. Results showed supervisor gender role attitudes predicted FSSB, as well as interactions of supervisor gender role attitudes with subordinate gender and occupational gender-type of subordinate. Findings suggest gender context of the work environment may override individual gender-role attitudes of supervisors when it comes to FSSB, and that men may experience lower FSSB than women in mixed-gender and male-dominated occupations. Implications for researchers and practitioners are discussed and include the importance of exploring possible structural changes in organizations to promote gender equality in FSSB.