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A student assessment system (SAS) must be fit for purpose to synergistically align with efforts at developing an equitable and high-performing education system. Transformational education reform is strongly desired in the Anglophone Caribbean; but SASs remain in a state of morphostasis, resistant to transformative change. This paper examines theory and strategies to guide assessment reform in the region, with Trinidad and Tobago used as a case study. Centred on decolonization theory, additional concepts are employed to conceptualize assessment reform for the Caribbean, including a typology of SASs, U-theory, and culturally sustaining assessment. Postcolonial SASs appear to serve specific legacy purposes but constrain equity outcomes. Moving towards a balanced SAS might be liberating and revitalising for these young societies.