Black female aspiring principals faced significant obstacles as they ascended to the principalship. This study chronicled the uncovering of the most common obstacles to representation, highlighting the importance of the findings. The problem explored in the research study was the underrepresentation of Black women as principals. The purpose of this qualitative phenomenological study was to explore Black women principals' lived experiences and the strategies they used to overcome barriers to principalship. The study's theoretical framework was the gatekeeping theory, a critical lens in examining gatekeeping practices during ascension. Two research questions guided the study: one focused on the lived experiences of Black women principals in overcoming barriers, and the second on the strategies Black women principals perceived as helpful in overcoming underrepresentation. The participants were ten Black female K-12 principals who were a purposive sampling, recruited via email and direct message on social media. The data collection process involved in-depth interviews. Reflexive thematic analysis and NVivo were used to develop data codes, categories, and themes. The categories were Black administrators treated differently and Black administrators hazed, which morphed into the theme of Black administrators mistreated. Also, the categories of barriers were entitlement and cherry-picking, principals, and PDT meetings, which led to the theme of barriers to the Black female principalship. Two key findings were that systemic gatekeeping practices and procedures hindered representation, and ten barriers and four strategies were identified. The study's implications for practice include professional development for principals, vigilance against gatekeeping practices, and strengthening administrative accountability. Recommendations for future research include exploring Black ascension trauma and self-care, ascension obstacles, and comparing studies of Black female principals' experiences. [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.]