Islands provide a place to conceptualise human-nature interactions in socio-ecological systems and to explore how such phenomena occur within decisive boundaries. Isolation, vulnerability to disruption, and constraints on the availability of natural resources add urgency to island sustainability questions with limited solution sets. This chapter presents findings that contribute to the larger issues of resiliency and vulnerability on islands. Cross-cutting reflections are offered based on studies conducted over the last 10 years at the Yale Center for Industrial Ecology of four diverse islands: Singapore, a highly developed island city-state; Puerto Rico, an island rich with nature and industry; O’ahu, a high density, tourism-dependent island, home to Honolulu, Hawai’i; and Hawai’i Island, also known as “The Big Island”, with a larger land area and a lower population density than O’ahu. Over the course of the twentieth century, each of these islands became heavily dependent on imports such as water, food, or fuel to sustain basic human needs and modern economic functions. Within the last decade, each has consciously sought to restructure its socio-ecological configurations by using more locally available resources in one or more of its metabolic linkages. This pattern has the potential to reconnect island economies with their natural systems while simultaneously enhancing relationships and increasing resilience.