The páramo is home to a significant proportion of global biodiversity and provides essential services for the development of life for millions of people in Ecuador. However, land use/land cover (LULC) changes threaten biodiversity and modify its functioning. The objectives of this study were: (1) to evaluate the conservation status of the herbaceous páramo (HP) ecosystem by analyzing its LULC in Ecuador’s southern region. (2) to identify possible regions where the native páramo ecosystem is being restored. We analyzed Landsat 8 images using Object-Based Image Analysis (OBIA) and a Classifier Decision Tree (CDT) to achieve these objectives. The results show that the native herbaceous páramo (NHP) ecosystem is being transformed into an anthropogenic HP (AHP). The area covered by the NHP ecosystem (296,964 ha) has been reduced by 50% (149,834 ha). Nevertheless, we identified five regions where the NHP is upgrading. These regions are relevant for studying NHP regeneration in Ecuador’s southern region, where soils are mostly andosols. The LU of the páramo, with cycles of exploitation, abandonment, and regeneration in a secondary páramo, is transforming the NHP ecosystem. These exploitation practices, global climate change, and lack of knowledge about the NHP ecosystem’s regeneration and its soils’ recovery threaten to substantially reduce the NHP area, its functionality, and its ecosystem services.