Although the Caribbean's Small Island Developing States (SIDS) minimally contribute to global greenhouse gas emissions, they face disproportionate climate risks and are particularly susceptible to systemic economic threats posed by climate change and subsequent increases in climate variability. Historically, strategic programs and investments have sought to develop more robust and adaptive engineered systems to absorb climate threats. However, such initiatives are limited and under‐resourced in SIDS’ context. This article reviews existing climate strategies in the Caribbean and then critically examines current gaps and barriers relating to climate impact knowledge, needs, and implementation. This examination can assist Caribbean SIDS leadership to identify opportunities to transition from a vulnerability‐reducing mindset to one of resilience and transformative adaptation to improve long‐term economic outlooks, social welfare, and environmental stewardship despite recurring and escalating climate risks.