Caribbean policymakers and regulators are grappling with the challenges and opportunities associated with the digital transformation, and seeking to develop inclusive, evidence-based policies suited to Caribbean realities. Realizing the need for data related to the digital transformation, efforts are ongoing across the subregion to improve measurement systems and agree on common indicators to enable national and subregional action. One of the outcomes of a 2023 subregional workshop on the measurement of the digital society to advance digital inclusion was a draft list of subregional priorities and indicators. As discussions on the list are set to continue, these areas and indicators warrant a closer examination, with the support of relevant data. This study seeks to contribute to the advancement of the discussions by providing an analysis of the current availability of data for the proposed priorities and associated indicators. The analysis is supplemented by information provided by Caribbean experts working with ICT policymaking and regulation regarding the strengths and weaknesses of their systems for measurement of ICT indicators, their related capacity-building needs, and their priorities for measurement. Finally, the study outlines some possible approaches to continuing the work of defining and refining the indicators in the future.