Despite comprising the majority of primary and secondary school teachers globally, women remain significantly under-represented in school leadership. To explore why this might be the case, this chapter delves into the nuanced personal and professional experiences of female principals in Catholic composite and secondary schools. The chapter sheds light on factors that influence women to pursue principal roles, the nature of female educational leadership and its challenges, the factors influencing the support and sustainability of female principals, and the expectations and demands associated with their roles in Western Australia, Australia. The positive attributes women bring to educational institutions constructively influence students’ academic and personal development; however, women’s leadership styles are significantly influenced by barriers such as conscious and unconscious gender bias and the balance between professional responsibilities and personal life. A notable barrier is the pervasive metaphor of the “glass ceiling”, which symbolises a hindrance to the upward progression of female leaders in the workplace. The study discussed in this chapter provides valuable insights that can promote the formulation of strategies for overcoming existing barriers to promote gender equity in school leadership and offers valuable recommendations for school administrators to bolster and empower future female leaders.