In the face of the increasing frequency of climate stresses, climate change projections can help in adaptation planning and resilience-building. However, typical climate change projections, such as annual average rainfall and temperature increases, are not helpful for farmers in understanding specific climate risks, like crop loss, and making adaptation decisions. Our study aims to identify and characterise context- and time-specific climate stresses in terms of climate conditions of concern to improve the understanding of future climate risks and enhance the climate resilience of semi-arid farming systems in India. Utilising the concept of critical climate-stress moments, we employ an innovative bottom-up methodology integrating insights from focus group discussions with farmers, key informant interviews, and an ensemble of downscaled and bias-corrected Coupled Model Intercomparison Project Phase 6 (CMIP-6) models. Our case studies include (i) a mixed crop-livestock farming system, (ii) a horticulture-based farming system, (iii) a cash crop–dominant farming system, and (iv) a cereal-dominant farming system. The specific climate conditions of concern identified were (i) increasing volume of late-monsoon rainfall, (ii) rising winter temperatures, (iii) increase in the number of days with temperatures exceeding 40 °C, (iv) increase in days with heavy rainfall (> 25 mm), and (v) increasing rainfall during the dry season. Identifying these critical moments improves understanding of both the temporal and spatial variations in climate risks, providing valuable inputs for targeted and implementable climate resilience–building actions. We recommend revising national and state action plans on climate change by utilising such region-specific assessments of critical climate-stress moments.