This instrumental case study investigates reasons behind female school principals resigning from their posts as school principals in Gauteng Province in South Africa. The qualitative study focused on the experiences of two purposefully chosen former school principals who resigned from their leadership positions before retirement. Data were collected through in-depth face-to-face individual interviews which were digitally recorded and transcribed verbatim by the researchers. Direct quotations were used to present the data, and these were thematically analysed using content analysis. The study established that female school principals in the study resigned from their positions because of individual, social and work-related barriers. Insidious, subtle, discriminatory gender-related practices and barriers that worked against the leadership of women were established. Key among these were jealousy, backbiting, rejection of female authority, lack of support from colleagues, lack of role models, isolation, discrimination and loneliness. These barriers were the same as those that contributed to the underrepresentation of females from positions of leadership as reviewed in the literature review. The study recommends a change of attitudes regarding leadership perception by individuals, society and organisations. While the findings of this study are useful in providing insights as is the case in most qualitative studies; the sample is rather small for generalisability. Hence it is recommended that future researchers could conduct large-scale research on this aspect.