The literature on smallholder farming and climate change adaptation (CCA) has predominantly investigated the barriers to and determinants of farmer uptake of adaptation interventions. Although useful, this evidence fails to highlight the changes or persistence of adaptation responses over time. Studies usually adopt a narrow focus on incremental actions that provide limited insights into transformative adaptation pathways and how fundamental shifts in policy can address the root causes of vulnerability across different sectors and dimensions. Drawing on an evidence synthesis commissioned by the International Fund for Agricultural Development’s Independent Office of Evaluation, this chapter outlines how lessons from CCA interventions can be transferred via three learning domains that are essential for transformational change: scaling-up (in its multiple forms), knowledge management, and the human-environment nexus. We discuss the implications of our findings on monitoring, evaluation, and learning, highlighting the challenges that evaluators may face in capturing (a) the persistence or durability of transformational pathways, (b) the complexity of “super-wicked” problems, and (c) the relevance of context-dependent dynamics, within a landscape setting. We also address the contribution of evidence reviews to contemporary debates around development policy linked to climate change and agriculture, and the implications and value of such reviews to provide independent scientific rigor and robustness to conventional programmatic evaluations.