The COVID-19 pandemic impacts have arguable been more pronounced in the developing world, such as the Small Island States (SIDS) of the Caribbean, where a plethora of geophysical and socio-political factors have led to increased vulnerability, particularly in fragile sectors such as agriculture. The pandemic added another layer of complexity to the unstable agri-food systems of SIDS in the Caribbean. Measures to contain the unfolding crisis have tremendously disrupted food systems by threatening the production, distribution, and marketing of commodities which exposed the frailty of the region's food security. Caribbean SIDS are highly dependent on food imports and relies on international markets to secure food. Many are also dependent on agricultural exports and have a large portion of their population involved in agriculture making them particularly vulnerable to the rigors of the pandemic. Export restrictions on foodstuff and prohibitions due to lockdowns and border closures further exacerbated these challenges. Additionally, food and nutrition security in the region is also subjected to the effects of climate change and climate-related disasters. Dealing with the impacts of co-occurring disasters is, therefore, an ever-present threat. This study examines the impact of COVID-19 on the agri-food supply in the Caribbean. It also identified measures and initiatives adopted to cope with these disruptive consequences. The study involves the use of internet-based surveys and focus group discussions and internet-based surveys with stakeholders and online searches for related literature. A total of 96 farmers, 60 food distributors, 84 food service operators, and 237 consumers from the region participated in the online survey and 4 focus group discussions between January and November 2021. The results confirmed that the impacts of the COVID-19 pandemic were evident along the entire agri-food supply chain and numerous challenges and shocks were identified across all participating groups and countries. Some challenges and shocks such as loss of income and related challenges including lower sales and loss of markets affected all groups in the study but to varying degrees and based on socio-demographic factors. In general people of lower income status and smaller businesses were more susceptible to the negative impacts of the pandemic.