This study evaluates the extent to which digital inclusion is considered in Caribbean digital transformation frameworks. Digital inclusion considers the ways in which digital divides are created as the digital transformation of society progresses, and how societal inequalities affect and are affected by digital technologies. As such, digital inclusion is a lens through which the effects of the digital transformation can be assessed. The study assesses the digital transformation policies of 11 countries and territories of the Caribbean and complements this analysis with qualitative data gathered through surveys and interviews from ICT focal points and policymakers in the region.