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The article evaluates the evolution of the Cuban economic reform embodied in the Guidelines on the Economic and Social Policy of the Party and the Revolution. Almost a decade after its approval, we assess progress and shortcomings while pointing out obstacles for the process to advance, together with suggestions on courses of action to continue the reform. After referring to previous attempts of economic change, we analyze the advancement of the Guidelines until 2019, a key year for Cuba since a new Constitution was approved. For this assessment were examined macroeconomic indicators, policy makers’ public discourse and academic papers published by renowned scholars of Cuban economy and society. The analysis of the international situation was considered with an emphasis on Cuba’s condition as Small Island Developing State –a factor that has often been underestimated by policy makers as well as by critics of the Cuban model.