Cyclones and other extreme events exert increasing pressure on South-East Asia’s societies and put smallholder farmers at risk. Here, we draw on participatory causal-diagramming workshops, interviews and survey data, to provide contextually grounded knowledge about rural communities’ exposure and vulnerability to climate-related hazards in western Myanmar. By tracing how the 2015 cyclone Komen led to a prolonged humanitarian disaster, we show that climate-related risks in this area arise from the complex interplay of households’ pre-existing vulnerabilities, persistent farming challenges, extensive disasters and cascading effects, which disparately affect lowland and upland communities. The different household strata’s dissimilar vulnerabilities vis-à-vis Komen’s impacts were rooted in the distinct exposure of their production systems to landslides and floods. Pre-existing land-access barriers, land-degradation processes, climatic stressors, agricultural pests and diseases, and chronic lack of assets and food insecurity further mediated households’ vulnerability. Relief interventions did not stop the disaster’s escalation, although this could have been achieved with early technical and material assistance to address the cyclone’s impacts on farmers’ land. Targeted aid for households facing imminent food insecurity or debt crisis could have lessened engagement in precarious coping strategies and distress migration. A diversification of households’ livelihood and land-use practices and increased redundancies of critical assets and infrastructure could help to mitigate future cyclone-triggered disasters. By demonstrating the strengths of local knowledge approaches in untangling the complex interplay of extreme events with households’ everyday vulnerabilities and agricultural land-use practices, we make a case for more contextually grounded disaster risk and climate adaptation research.