The focus of my chapter in the 2014 edition of the Springer International Handbook of Educational Leadership for Social (In)Justice was teacher leadership and the importance of teachers as change agents in the transformation of the South African schooling system. The main finding was that the activist identity of the school leader, necessary for the creation of a successful democracy, remains a pipedream in the majority of South African schools. The closing question posed in my 2014 chapter was: How do we stimulate the activist identity in teachers in order for them to become transformative leaders who can lay the groundwork for challenging social inequities and inequalities in schools? This question served as the research question for the new study on which this updated chapter is based. Designed as an exploratory case study, the new study drew on the experiences of teachers and school leaders involved in a South African university postgraduate qualification in Educational Leadership and Management. The degree is deliberately designed as a transgressive service learning course in the critical research tradition. The 2023 cohort formed the case, and all 20 graduated students were invited to participate in the study. Ten of the twenty students accepted the invitation. Critical pedagogy provided the metatheory for the study, with critical educational leadership and transformative leadership as the substantive theories. Data generation tools included individual semistructured questionnaires and a focus group interview. Data were analyzed using an open method of coding to identify common themes and patterns of difference. Thereafter, the theoretical principles of the analytical framework were applied to the data. The chapter demonstrates the potential of a transgressive university service learning course in disrupting school leadership myths and enabling the leadership development of teachers and learners. Additionally, it provides a global south critical educational leadership study based on empirical evidence.