This qualitative research study described African American female secondary educators’ challenges in their educational working relationships. The purpose was to truly understand the challenges that African American female secondary teachers experienced in the classroom, outside of the classroom, in their dealings with their students’ parents, colleagues, and their relationships with school administrators. This study focused on the challenges 10 African American female secondary teachers encountered in their educational work environment. This study also took into account how those teachers’ relationships with their students’ parents, colleagues, and administrators affected the teacher/student relationship. In an effort to increase student achievement, researchers, educators, students, parents, and administrators must all work closely to improve relationships between teachers and students within their district. Moreover, district policies must continue to encourage the development of schoolamily-community collaboration as an essential component vital to student academic improvement efforts. Administrators must continue to equip African American female secondary educators with a range of practices for involving students, parents, colleagues, and administrators to improve student outcomes. The best efforts are comprehensive, seeking to involve all teachers, students, parents, their colleagues, and administrators in a variety of roles. African American female secondary teachers can be empowered through training, time, and support. There are long-lasting, long-term investments in cultivating positive relationships between teachers and students that will help students reach their full potential. The cost in terms of student outcomes not achieved is incalculable.