jats:pCurrent adaptation theory tends to consider individual buildings or the city level, which cannot address decisions related to masterplan developments on large brownfield sites. This paper investigates the drivers for building demolition or retention and adaptation decisions at the masterplan scale. Expert interviews and three case studies are used to explore how and why decisions to demolish, or to retain and adapt, are made at this scale. The research compared three different geopolitical contexts: Cambridge in the UK; Eindhoven in the Netherlands; and Sydney in Australia. Additional factors and complexities that should be considered at the masterplan scale are identified. The theoretical underpinnings of urban development processes are used to explain these complexities in relation to four existing models and demonstrate that no one model is adequate to describe the interactions. With increasing awareness of climate change impacts, it is critical that demolition decisions on masterplan developments are reviewed in the light of retaining carbon as well as heritage. Practice relevance This research demonstrates the different and specific concerns applying to demolition and retention on masterplan scale sites compared with the individual building scale. Although the evidence shows that decisions are context specific, the criteria as identified and categorised within this research offer a useful tool for stakeholders when establishing their priorities and approaches to decisions to demolish or retain and adapt within a masterplan context. This should help to avoid contested decisions and can help community groups hoping to have an influence over the long-term decisions, as well as developers looking to retain good relationships with the local community. The identified criteria can support planners and local authorities responsible for approving masterplan developments to better understand the factors relevant to each decision, including the importance of retaining flexibility throughout to enable response to changing circumstances.</jats:p>