Food insecurity, obesity, and non-communicable diseases (NCDs) are significant problems impeding human and economic development of small island nations and communities of the Caribbean Region. In addition, the Caribbean Community states remain prone to natural disasters and extreme weather events occurring at an increased frequency, attributed to climate change. Concerted efforts, increasing political commitment and leadership to address food insecurity and nutritional challenges during the past two decades enabled several regional and international policies and initiatives with varying levels of success. These initiatives recognize that the healthiness of local diets is ultimately determined by the local production capacity, the availability of and access to healthy foods, and its market characteristics including the importation and proliferation of unhealthy processed foods. This was emphasized during the recent United Nations Food Systems Summit convened to set the stage for global food systems transformation to achieve the Sustainable Development Goals by 2030. Canada’s International Development Research Centre (IDRC) has been supporting the development of evidence, innovation, and policies to build healthier food systems, enable nutritious and sustainable diets, and prevent NCDs. IDRC’s recent contributions in the Region include two projects supported between 2014 and 2018. First, the Farm to Fork project, under the flagship Canadian International Food Security Research Fund in collaboration with Global Affairs Canada, sought to improve the nutritional outcomes of primary school children in St. Kitts and Nevis by supporting local food production by smallholder farmers, and by enhancing the local supply chain from production to consumption. The second was the Port of Spain Declaration Evaluation project which assessed the impact of a 2007 declaration by Caribbean heads of government to address the epidemic of NCDs in the Region. A review of lessons learnt from both projects observed that integrated interventions with a food systems approach to leverage both agricultural and public health agendas towards improving the production and consumption of local healthy foods with due consideration to gender hold promise for improving food security and for preventing NCDs. To test this integrated approach, IDRC support from 2018 to 2022 to researchers from the University of the West Indies and their partners involved investigating the structural, policy and behavioural conditions which drive food production and consumption by focusing on three countries (St. Kitts and Nevis, St. Vincent and the Grenadines, and Jamaica). Their findings, partly captured in this special issue of the Pan American Journal of Public Health, reveal the challenges to address the complex causal pathways that culminate in the high burden of overweight and other diet-related diseases. The size of small island states makes their food systems no less complex. A causal loop diagram generated by the project team at the beginning of the research using a participatory approach clearly depicts the complexity of the problem including multiple drivers of unhealthy eating. This multidimensional project has faced this challenge of complexity and attempted to bring some coherence to the many changes and interventions required for improved outcomes. The articles in this special issue mostly reflect the initial research outputs of the project that describe the food system and identify opportunities for policy change and program development. The research underscored the importance of a multi-disciplinary and multipronged approach to test interventions from different entry points. The interventions were therefore not pre-defined at the outset. Further research on the tested interventions will also soon be available, despite some limitations created by the disruption of the COVID pandemic. Led by regional and national teams, the researchers successfully brought together expertise and stakeholders in health, agriculture, gender, policy, civil society and business. This reflects an increase in regional and local leadership, critical to translate the research findings into useful policies and interventions. This will pave the way for the sustainable promotion of healthy diets and control of NCDs in the Caribbean. Though there is no one solution or ‘silver bullet’ for creating an enabling environment in the food systems for healthier diets, several opportunities and approaches are presented in this special issue.