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Caribbean student assessment systems (SASs) are dominated by public examinations at 11+, 16+ and 18+, minimizing large-scale learning and formative classroom assessments. Current Caribbean SASs replicate colonial designs and intentions. What explains the stability of the system and how do we theorize on sustainable future change? Caribbean SASs appear fit for purpose in plantation economies but not knowledge economies. Decolonization theories (DTs) present a unique and varied framework informing the direction of assessment reform for sustainable Caribbean futures. DT is cultural, psychological, and economic freedom achieved through dismantling structures, institutions and values for continued hegemony of colonial legacies. DTs conceptualize iterative or radical change but identify goals that go beyond equity, such as liberation, justice, and citizenship.