Although there have been significant increases in the number of female school leaders over the last several decades, women are still drastically underrepresented in the ranks of school and district leadership positions within K-12 school systems. The purpose of this qualitative case study was to examine and understand female school administrators' perceptions of both internal and external barriers in attaining K-12 school administrative positions. The findings are reported in four distinct areas: internal barriers, external barriers, unique experiences of female Latinx/Hispanic leaders, and advantages of being a female school administrator. The eight study respondents included site principals, district office directors, assistant superintendents, and one current superintendent. Semistructured interviews were conducted virtually with each participant. The interviews provided a framework for analyzing and reporting the journey and lived experiences of each respondent. The rich narratives that surfaced documented how each woman overcame gender-based challenges from within their own family, gendered societal norms, and workplace. Implications include restructuring district recruitment/hiring procedures, examining time expectations for school administrators, offering professional development for district staff members, and implementing meaningful mentoring opportunities for women. [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://www.proquest.com.bibliotheek.ehb.be/en-US/products/dissertations/individuals.shtml.]