AbstractMany social-ecologically sensitive Small Island Developing States (SIDS) increasingly face global (climate) change risks to sustainable development. However, the validity of factors said to contribute toward vulnerability is disputed in light of the differing economic success, enormous heterogeneity, divergent paths of development, and varying potential for adaptability displayed by small islands. Research on uncertainty, vulnerability and resilience of coupled social-ecological systems (SES) can provide a valuable contribution to the sustainability debate. Based on the fundamentals of complexity theory, the notions of social-ecological adaptability, and panarchy, this article highlights the role of context-based, hybrid, and limited environmental knowledge and risk knowledge systems and cultures. The modes of organization of disaster management in Grenada (Eastern Caribbean) and environmental governance in The Bahamas (Western Caribbean) on various spatio-temporal scales serve as case studies. The production and communication of knowledge, the difficult (cross-scale) integration of diverse knowledge systems, the role of experience and memory, as well as social/institutional learning and inertia appear as significant factors as regards the strengthening of social adaptability. The findings further demonstrate that significant challenges remain for Caribbean SIDS. These include long-term, socially, locally, and sectorally differentiated vulnerabilities; deficits in governance and communication; and the diverging and spatially-temporally bounded nature of knowledge systems.