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This paper pulls from a larger ongoing research project funded by the Spencer Foundation with researchers in three public universities across Canada. The project takes a decolonizing, transnational gaze into the work and wellbeing of Black school leaders (school principals and vice/assistant principals) in five Canadian provinces and two Caribbean countries, namely British Columbia, Ontario, and the Prairie Provinces Alberta, Manitoba, and Saskatchewan, and Grenada and Jamaica. We draw on document analysis of mainstream leadership frameworks and policies and one-on-one and small-group conversations with school leaders across these sites. In this paper, we present preliminary findings from our two Caribbean sites, Grenada and Jamaica, illuminating how colonial structures and ideologies perpetuate racial inequities for Black school leaders in these contexts.