Historical analogies of environmental change and stress are a well-established method of examining vulnerability to the impacts of climate change. Understanding the present by examining the past can uncover deeply seated values, norms and worldviews that continue guide our actions and planned adaptations to climate change. In this presentation we draw on the historical example of the environmental transformation of Aotearoa New Zealand from predominately woodlands into farmlands; a transformation which was inextricably linked with the social transformation of indigenous Māori society following European colonisation. The case study illustrates how both incidental and purposeful transformations can be instigated by small groups of committed individuals working in formal or informal networks. Such changes however can also be imposed by outside experts who institute widespread changes under notions of progress and improvement without local support. Such transformations involved widespread changes to Indigenous governance regimes, agricultural systems, production and consumption patterns, lifestyles, values and worldviews, and inevitably involved both beneficial and negative outcomes for local peoples. We argue that historical analogies are an important analytical tool in understanding the roots of present and potential future vulnerability. Such methodological tools present an opportunity to assess the processes that shape vulnerability, resilience, and ultimately the adaptation pathways that societies decide to or are embarking on. Ethically informed adaptation therefore relies on a holistic understanding of those values and visions, which have and which continue shaping our notions of ‘successful’ adaptation.