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This study seeks to identify and examine the challenges that female principals experience. Women are slowly climbing the promotional ladder within education, yet they experience many challenges. The fact that society has the perception that women are mothers and caregivers does not make the advancement of females easy. Although the GETT report (1996) made recommendations to ensure equality in education females are still vastly under-represented in managerial positions in education. The study was conducted from a feminine perspective. It is a qualitative case study and individual interviews, a focus group interview, observation and field notes were used to collect data. A total of three females were included in the study. Participants were purposefully selected. Two of the participants are from disadvantaged schools while the third one is an ex-Model C principal. A consent form was sent to all the participants, covering all ethical issues of voluntary participation, confidentiality and anonymity. The main question was the challenges faced by female managers in education. Having spent time with each of the principals the data in the form of field notes and transcripts were analysed. It was found that the three principals experienced similar challenges. Their responses did not always reflect what the literature said regarding the challenges. All three principals felt that more formal support structures from the DoE is needed. They mentioned that the following could be implemented to ensure that they are more effective and better prepared to face these challenges: Workshops; Mentoring and Networking; Financial Assistance; and, Capacity Building