Promoting climatic resilience in production systems is key to ensuring their sustainability in the face of ongoing climate change. Forest plantations have proven vulnerable to compound events of drought and heatwaves, although vulnerability varies depending on the ecohydrological characteristics of the landscape. We present case studies in which satellite imagery and Earth observation products were used to identify landscape units that reduce pine plantation mortality at local and regional scales. We focused on an unexpected, regionally distributed tree mortality event that occurred in commercial Pinus species in the most important forestry region of Argentina during the 2021–2022 warm season. This hotter-drought event followed three consecutive years of drought. Using Sentinel-2 imagery, we estimated canopy mortality between November 2021 (first field mortality observations) and October 2022 in Pinus spp. plantations established across the Mesopotamian region in the N.E. of the country. Our analysis revealed that spatio-temporal heterogeneity in canopy mortality was strongly associated with landscape features related to ecohydrology. Mortality was higher, earlier, and progressed faster in shallow soils with likely limited and short-lasting water availability. In contrast, mortality was near zero in depressed, waterlogged units. Intermediate levels were observed in areas with shallow water tables, where trees developed shallow root systems. These results suggest that landscapes allowing for deeper root development and/or longer-lasting soil water availability may be more suitable for drought-resilient pine plantations. Additionally, this approach helped identify areas with low crop production potential and/or high importance for biodiversity conservation, offering valuable insights for sustainable land-use planning at landscape and regional levels under climate change.