Climate change and its interactions with complex socioeconomic dynamics dictate the need for decision makers to move from incremental adaptation toward transformation as societies try to cope with unprecedented and uncertain change. Developing pathways toward transformation is especially difficult in regions with multiple contested resource uses and rights, with diverse decision makers and rules, and where high uncertainty is generated by differences in stakeholders’ values, understanding of climate change, and ways of adapting. Such a region is the Murray-Darling Basin, Australia, from which we provide insights for developing a process to address these constraints. We present criteria for sequencing actions along adaptation pathways: feasibility of the action within the current decision context, its facilitation of other actions, its role in averting exceedance of a critical threshold, its robustness and resilience under diverse and unexpected shocks, its effect on future options, its lead time, and its effects on equity and social cohesion. These criteria could potentially enable development of multiple stakeholder-specific adaptation pathways through a regional collective action process. The actual implementation of these multiple adaptation pathways will be highly uncertain and politically difficult because of fixity of resource-use rights, unequal distribution of power, value conflicts, and the likely redistribution of benefits and costs. We propose that the approach we outline for building resilient pathways to transformation is a flexible and credible way of negotiating these challenges.