The very ‘insularity’ of islands makes them excellent focal points for sustainability studies that systematically analyze the interactions between human activities and the environment. In this chapter, we seek to explore the factors that cause island societies to prosper and sustain themselves and those that lead to collapse. A number of historical cases of collapse have occurred on the island we investigate (Samothraki, Greece) in the sense of a breakdown of social complexity and rapid population decline. At present, there is a fragile situation of slow population decline and ecological challenges that might be brought to a ‘tipping point’ by the impacts of the Greek economic and governance crisis and by climate change. The island community has decided to make an effort to turn the whole island into a Biosphere Reserve by UNESCO standards. Building upon a sociometabolic understanding of socioecological systems and using systems thinking (and, to a certain degree, modeling), we attempt to identify environmental and social ‘tipping points’ for Samothraki. Moreover, in line with the Long-Term Socioecological Research (LTSER) tradition, we argue that analyzing society-environment relations for different phases of the island’s history and gaining insights from past collapses can help to identify threats and possible ailments. Finally, this chapter will reflect not only on the outcome but also on the process of performing transdisciplinary research, that is, research that aims to achieve a practical outcome.