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In responding to the need for leadership preparation, the South African National Department of Education has introduced the Advanced Certificate in Education (School Management and Leadership). This is a necessary initiative considering that principals are not required to have any formal leadership qualification. The Advanced Certificate in Education, however, has seemingly not taken into account the particular challenges experienced by women principals. While women dominate the teaching profession, they encounter immense challenges in accessing, and asserting their positions of leadership. The paper, firstly, seeks to understand the tension between women principalship and male stereotypes of leadership. Secondly, by drawing on the experiences of female principals, it hopes to offer some recommendations towards improving the Advanced Certificate in Education.