This paper interrogates the aspects of islandness labelled “vulnerability” and “resilience” through analysing the concepts’ definitions from a development perspective. The investigation is conducted through the lens of four assumed islandness aspects: boundedness, smallness, isolation and littorality. Discussion examines how and why core concepts of vulnerability and resilience have emerged from island studies, demonstrating how these two aspects of islandness are socially and culturally constructed, can influence development approaches taken and are enhanced by island geographies. Insights from island geographies, and comparing island and non-island perspectives, show how manufactured islands of vulnerability and resilience can slant discourses and reinforce stereotypes. Island geographies in their diversity teach that vulnerability and resilience, being neither opposites nor independent variables nor objective variables, are most supportive of island development endeavours when accepted as being subjective, contextualised and nuanced. The lessons yield advice on ensuring that development contexts for vulnerability and resilience are widened and deepened, drawing strength rather than constraints from the four assumed aspects of islandness. Within boundedness, smallness, isolation and littorality, the two aspects vulnerability and resilience can be empowering and disempowering for development.