Purpose: The purpose of this qualitative study was to explore the experiences of women high school principals to uncover challenges contributing to the underrepresentation of women in secondary school leadership. Moreover, this work is situated within the larger movement of educational leadership for social justice, with a focused application of a feminist theory lens and Social Role Theory. The two research questions that guided this study were: (1) How do select high school principals who are women describe their lived experiences in the principalship? and (2) What do these select high school principals who are women believe contributes to the underrepresentation of women in high school principal positions? Methodology: A phenomenological approach was chosen to explore the lived experiences of seven current high school women principals in Texas. The transcendental phenomenological research approach proposed by Moustakas (1994) was employed. Transcendental phenomenology has been summarized by Moustakas as "a scientific study of the appearance of things, of phenomena just as we see them and as they appear to us in consciousness" (1994, p. 49). Women principals who have led at their current school for at least three years were the focus of the study because they have demonstrated an ability to navigate the leadership role. Data in the form of background questionnaires and individual interviews from seven women high school principals were collected and reviewed. Findings: Each participant described specific experiences, as a woman, serving in the role of high school principal. In this study, four common themes emerged: (a) Servant Leadership, (b) Facing Barriers, (c) Support Systems, and (d) Advice. Moreover, participants described the challenges they faced during their tenure as high school principals, and strategies they used to overcome the challenges. Additionally, participants expressed gender bias, a glass ceiling, and family responsibilities as most damaging to women for career progression, and thus underrepresentation in the high school principalship. [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.]