There is increasing interest in transformational adaptation to climate change in agriculture, i.e. adaptation that involves large-scale, novel responses to reduce vulnerability to climate risks. Transformational adaptation is less well understood than incremental adaptation, since there are few studies of agricultural enterprises making transformative changes in response to climatic change. This paper is an in-depth study of an agricultural company’s attempt to implement transformational adaptation in response to climate change. We document the Peanut Company of Australia’s (PCA) response to predicted climatic change by expanding its operations into Katherine, Northern Territory, after decades of below-average rainfall in their traditional production region in south-east Queensland. Our research question was: what conditions and processes influenced the outcome of the company’s response? We conducted 37 semi-structured interviews with company, government and community representatives to examine diverse perspectives on PCA’s expansion into Katherine and its subsequent strategic retreat. To reveal insights into why, when and how this attempted transformational adaptation occurred we reviewed the literature and identified Park et al.’s (2012) Adaptation Action Cycles (AAC) framework and aspects from the organisational adaptation literature as useful for our analysis. Based on our findings, we revised the AAC framework to better reflect the way that incremental adaptation in situ can occur simultaneously with transformational adaptation at a new location. Our study illustrates that transformational adaptation in agriculture is difficult, complex, risky and costly and sometimes unsuccessful, revealing some of the challenges of and barriers to organisational adaptation in agriculture, especially when moving to a new location.