The economic challenges in the Caribbean can be linked in significant measure to the region’s external vulnerability. This paper looks at trends in financial flows in the context of the region’s need to strengthen its resilience. It starts by focusing on three concepts: vulnerability, fragility and resilience-building. Vulnerability is looked at as a ‘structural’ variable, dictated by geography and reinforced by economic forces. Fragility is looked at as a ‘process’ variable, a recurring feature of the workings of the institutions, underscored by a shortage of resources, and missing systems for accountability and effectiveness in delivery. Building resilience in Caribbean economies is the most challenging variable – to generate a net inflow of funds, sustain competitiveness and grow the wellbeing of their citizens on a persistent path.