The positive balance of Cuba’s social indicators in comparison with countries having similar, and even considerably higher, GDP is acknowledged by the most influential international organizations despite disagreements with the political structure of the country. Analyzing the experiences, shortcomings and challenges of the educational strategies in Cuba and their impact in poverty alleviations is a complex endeavor; research literature on this subject is considerably scarce. In addition, the analysis of the “Cuban case”, in whatever respect we deal with, is often polarized and one might argue, biased by researcher’s perspectives, often of political dimension.

The aim of this book chapter is to bring forward a number of issues (highlights) to be considered in creating an analytical framework for the experiences, shortcomings and challenges of Cuba in the search for poverty alleviation via education. In pursuit of its aims, the chapter initially presents a number of key framing contextual issues to be considered when analyzing any dimension of Cuban social reality including education and poverty alleviation. It goes further analyzing educational developments and experiences which are at the bottom of poverty alleviation strategies and finally concludes with a presentation of the perceived challenges. The paper raises different questions and provides not answers but perspectives which might contribute to the further research that is due.