The states of the CARICOM and OECS Caribbean are small island developing states (SIDS) which are exceedingly vulnerable to economic and ecological shocks. Examples of vulnerability are the economic cost of a heavy reliance on imported oil & gas resources, and the pernicious effects of climate change. A key strategy to mitigate these vulnerabilities is to invest in renewables, increase resilience, and effect an energy transition for the Region.However, research and data on renewable energy and resilience in the region is still evolving. Further, it has become apparent from stakeholder fora such as CREF and IRAC that there are certain fundamental elements which need to be understood and addressed before the Region can achieve a just energy transition. The first is a clear understanding of what resilience means for the Region's renewable energy sector. The second relates to financing options which incorporate elements of resilience into renewable energy projects. Thirdly, in the rebuilding from the COVID-19 pandemic, it is recognised that reimagining full gender equality in the energy sector will be key to sustainable and competitive development.This Article explores the recent developments to re-imaging the route to resilience and renewables in the CARICOM & OECS Caribbean through collaborative efforts at the regional level. It also sets out the next steps in these three fundamental areas and outlines the role for future research to support these regional initiatives.