Despite several initiatives to promote gender equality in leadership, women remain under-represented in South African higher education, particularly in senior leadership positions. Gender bias, cultural norms, institutional barriers, and the difficulties women experience in balancing work and personal commitments continue to hinder women’s advancement into leadership roles. It is notable, however, that whatever improvements have been made are largely due to the effects of programmes such as Higher Education Resource Services South Africa, the Employment Equity Act, and the National Plan for Higher Education. The purpose of this chapter is to determine the extent to which these supportive programmes have promoted gender equality and inclusive leadership. Through an examination of the data, this chapter identifies recurring challenges and provides insights into how policies might further support change in higher education leadership. It is hoped that the chapter will contribute to ongoing improvements in gender equality by drawing attention to issues that need attention to bring about lasting equality in the higher education setting.