This qualitative case study explored the perceived barriers to leadership for female-identifying student affairs professionals at the midlevel who aspire to, but have not yet attained, a senior student affairs officer role. Women hold 71% of all student affairs positions in higher education compared to men; however, that majority shrinks to 56% for senior-level positions (Pritchard & McChesney, 2018). Thus, a study designed to explore gendered barriers to leadership was warranted. The research questions were designed to explore what barriers, if any, have participants experienced regarding their ability to move into a senior student affairs officer role and to what extent, if at all, participants experience higher education institutions as gendered organizations. A theoretical framework of gender role theory and gendered organizations was used to explore the research questions. The study was conducted in two phases; Phase 1 included a questionnaire in which participants (n = 32) responded to a series of statements about perceived barriers to leadership and gendered workplaces in student affairs. In Phase 2, follow-up interviews were conducted on a random selection of participants (n = 8) from Phase 1. This study used a theoretical framework that combined the theories of gender role congruity (Eagly & Karau, 2002) and gendered organizations (Acker, 1990), which provided the context for investigating the role structures of the organizations in which participants worked and how social roles impact women's paths to leadership within student affairs. Findings from the study indicated three themes related to personal barriers, which were impostor syndrome, work-life conflict, and showing emotion is unacceptable. Findings also revealed sociological barriers that included the nature of student affairs work, saying yes to everything, and religion's influence on gender roles. Implications for practice, as suggested by participants, were a move to more flexible policies about work hours and locations, providing networking and mentoring opportunities, teaching men to be allies to women, and professional development opportunities focused on developing leadership skills. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://bibliotheek.ehb.be:2222/en-US/products/dissertations/individuals.shtml.]