The integrated regional energy policy and planning (IREPP) framework was devised to evaluate the feasibility of energy policies in meeting declared national targets. While the framework advances the comprehensiveness of the feasibility assessment by bringing in concepts like environment economic equity, the muted way in which institutional factors and capacity are addressed remains weak and ineffective. Here, we corrected this weakness by presenting an IREPP framework that is enhanced by integrating principles of the institutional assessment and design (IAD) framework. The IAD framework emphasizes the careful consideration of contextual factors, it draws attention to the full range of transaction costs, and does not presume a priori that one type of institutional arrangement. This IREPP-IAD framework was used to evaluate the feasibility of energy policies in three different island jurisdictions—Taiwan, Mauritius, and Trinidad and Tobago. With ambitious national targets, these islands are good testing grounds for this updated approach. Through qualitative comparative case study analysis, several institutional factors were found to play an influence if national energy policies are likely to meet set targets. These factors included: government/policy decision makers and the decision/policymaking environment; governance structure and commitment for energy policy; existing policy instruments and tools that are in play and those planned; polycentricity; stakeholder participation and community building; market dynamics; information transparency; pilot programs and technology innovations/research; compliance or responsibilities under the Paris Accord; grid connectivity and monitoring of the policy implementation progress. This study contributes in two ways. First, by providing a more robust framework for assessing institutional arrangements that moderate how energy policies are implemented and second, providing insightful assessments of the energy policies in three island jurisdictions, thereby increasing our understanding of island energy policymaking and implementation in these understudied geographies.