This book examines the policy outcomes of purportedly unavoidable tendencies towards educational isomorphism and harmonization by analyzing, at a regional level, the educational policies devised and carried out by the Caribbean Community (CARICOM) over the past two decades. It chronicles the policy process (functional cooperation) and policy tools (lessons-drawing, externalization and policy transfer) of regionalization and highlights, from a cooperation and collaboration perspective, the importance of time, space, and geographic proximity and their roles in furthering convergence. The book’s analyses conclude by showing that, based on the semantics of harmonization, educational isomorphism occurs in cyclical waves and that the fifteen member states of CARICOM only cooperate when it is in their best interest, irrespective of the policy outcome. Therefore, the isomorphic tendencies that exist at the regional level are not – or not primarily – the result of a world polity as hypothesized by neo-institutionalist theory, but rather that of collective choices to confront both challenges and opportunities of globalization and global competition.