Historical analogies of social transformations can be used to identify what factors are conducive to transformation in the context of climate change. Through a series of case studies from Oceania we examine how the widespread environmental and social changes associated with European colonisation in the nineteenth and twentieth centuries resulted in multiple transformations. Diverse examples, ranging from environmental transformation in New Zealand, to social transformation in Australia, and political transformation in Vanuatu, highlight how transformation is often not a rapid or singular event, but rather is a cumulative and incremental process. These case studies provide us with an opportunity to consider both the circumstances under which transformation occurs and the long-term consequences of transformation. While purposeful transformations can be instigated by small groups of committed individuals working in formal or informal networks, our case studies highlight that deliberate transformations are often imposed on societies and result in the loss of resilience, increased vulnerability, and the creation of new risks within socio-ecological systems. Keywords: historical, indigenous, colonial, incremental, transformative