Lowland areas depend on water flowing from distant headwater regions, while Andean cities and communities are situated at these headwaters. As a result, they rely on water sourced from small catchment areas, making them particularly vulnerable to shifts in the hydrological cycle and changes in land use. Tropical Andean ecosystems, such as paramo and cloud forests, have historically provided a reliable water supply for downstream communities. However, recent shifts in land cover, land use practices, and erratic weather patterns are increasingly threatening this water supply. This study highlights some of the most urgent challenges to water security in tropical Andean communities, focusing on issues like deforestation, wetland drainage, road construction, rainfall-triggered landslides, and the construction of future dams. The city of Cuenca in the southern Andes will serve as a case study. Additionally, aging water infrastructure combined with rapid urban growth is driving an increased demand for water. This dual pressure is leading to significant conflicts among water users. Addressing these challenges requires an interdisciplinary approach to water and land use management.