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Jamaica’s education system reflects its colonial history in its classification and treatment of certain students within specific schools (Author & Author, 2022). Furthermore, school leadership remains ill-equipped to challenge power within and beyond schools (MacDonald, 2020) and how it affects student achievement. Therefore, this case study explored Jamaican principals’ social justice (SJ) beliefs and actions and their perceptions about the influence of their principal preparation on those SJ beliefs and actions using semi-structured interviews, photo-elicitation, and document analysis. The three main themes perceptions, possibility, and purpose underscore the importance of critical dialogue in shaping principals’ SJ understanding and leadership practice. Moreover, the study’s findings have implications for school leadership, education policy, and leadership preparation in Jamaica.