Timely crop planting is a foundation for climate-resilient rice-wheat systems of the Eastern Gangetic Plains—a global food insecurity and poverty hotspot. We hypothesize that the capacity of individual farmers to plant on time varies considerably, shaped by multifaceted enabling factors and constraints that are poorly understood. To address this knowledge gap, two complementary datasets were used to characterize drivers and decision processes that govern the timing of rice planting in this region. The first dataset was a large agricultural management survey (rice-wheat: n = 15,245; of which rice: n = 7597) from a broad geographic region that was analyzed by machine learning methods. The second dataset was a discussion-based survey (n = 112) from a more limited geography that we analyzed with graph theory tools to elicit nuanced information on planting decisions. By combining insights from these methods, we show for the first time that differences in rice planting times are primarily shaped by ecosystem and climate factors while social factors play a prominent secondary role. Monsoon onset, surface and groundwater availability, and land type determine village-scale mean planting times whereas, for resource-constrained farmers who tend to plant later ceteris paribus, planting is further influenced by access to farm machinery, seed, fertilizer, and labor. Also, a critical threshold for economically efficient pumping appears at a groundwater depth of around 4.5 m; below this depth, farmers do not irrigate and delay planting. Without collective action to spread risk through synchronous timely planting, ecosystem factors such as threats posed by pests and wild animals may further deter early planting by individual farmers. Accordingly, we propose a three-pronged strategy that combines targeted strengthening of agricultural input chains, agroadvisory development, and coordinated rice planting and wildlife conservation to support climate-resilient agricultural development in the Eastern Gangetic Plains.