’Triple-wins’ has emerged as a powerful rhetorical device for instigating responses to linked climate-development challenges. By promising to deliver synergistic mitigation-adaptation-development outcomes via a single intervention, triple-win logic has proven immensely appealing to policymakers and researchers alike. Although heralded by its proponents as an enabler of transformational change towards desirable low-carbon and climate-resilient futures, emerging critiques suggest focus upon triple-wins detracts attention from pressing social questions pertinent to integrative efforts, including how trade-offs are deliberated, for whom wins and losses accrue, and who decides. Here, we review emerging critiques of triple-win rhetoric within climate-smart agriculture and climate compatible development, and explore its suitability as a device for enabling transformational change. We argue that triple-win rhetoric, as currently conceived, fails to engage with the social complexities inherent to the pursuit of integrated outcomes, as well as the underlying social conditions that perpetuate business-as-usual development. In response, we propose a more dynamic ‘pathways’ approach to triple-wins that foregrounds normative commitments to recognition, rights and justice in the pursuit of desirable climate-resilient futures.