The purpose of this basic qualitative study was to examine how mentoring support systems, race and gender intersectional challenges shape the pathway for five African-American women principals in a South Texas urban school district. The researcher used a semi-structured interview question protocol, audio-recorded, and professionally transcribed the interview data. The results revealed that each of the principals experienced race and gender intersectional challenges but fulfilled their role and responsibilities despite these challenges. For these five principals, the district's mentoring support system did not offer the necessary support that the principals needed and desired. Finally, after the researcher analyzed the data and used NVivo qualitative analysis software, themes on questionable leadership abilities of the principal, race and gender intersectional challenges, and mentorship experiences, formal and informal, emerged. [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.]