The rubber boom across much of Southeast Asia has led to environmental destruction, and the resultant crash in the price of rubber has destabilised livelihoods. We investigated the necessary factors required to enable a transition towards a more sustainable model for rubber cultivation in Southwest China (i.e. the ‘greening’ of rubber cultivation), using a framework for the integrative study of multiple aspects in complex land use issues. We present findings from stakeholder interviews and a stakeholder workshop, and discuss their relevance within and beyond Southwest China. The current focus of researchers and development practitioners tends to be on finding technical solutions to address unsustainable rubber cultivation practices. However, stakeholder consultations revealed that the key barriers were more social: low levels of trust and knowledge exchange between stakeholder groups and fragmented visions about the future of the landscape. It is very important to continue the economic prosperity initially brought by rubber, but, without improved communication between government and researchers and smallholder farmers, this will be very difficult to achieve. A wider landscape perspective is needed to address issues in rubber cultivation to avoid repeating the same problems of cash crop boom and bust experienced with other crops, most notably bananas. We conclude that more effort should be put into developing mechanisms that integrate technical knowledge, enhance social relationships, and present a forum for reconciling – or at least acknowledging – the differing needs, knowledge, and objectives of different groups, and transcending the power dynamics between smallholder farmers and government and researchers.