Ciénegas are rare wetlands in arid landscapes of the North American Southwest, historically providing critical ecological and hydrological functions but increasingly threatened by changing climate and land use pressures. This study quantifies changes in ciénega condition and floodplain dynamics using a state-and-transition model (STM) informed by expert knowledge and remote sensing. Key factors include woody plant encroachment, water availability, and soil aggradation. We mapped 31 ciénegas with high-resolution imagery and analyzed Landsat data (1985–2023) to assess vegetation health and moisture using the Normalized Difference Vegetation Index (NDVI) and Normalized Difference Infrared Index (NDII). Results show substantial interannual variability in phenology, water stress, and soil moisture, with regional drying and elevation strongly influencing ciénega resilience. We classified ciénegas into three functional states—healthy, desiccated, and dormant—and mapped their 2023 condition. Trend analyses indicate most ciénegas exhibit greening despite drought, though localized variability underscores the need for site-specific management. None are in a stable climax (reference) state; rather, they transition among states in response to external drivers. Increasing woody plant cover and surface drying, likely linked to declining regional water tables, favor deep-rooted species over wetland grasses—a pattern mirrored in adjacent control plots. Spatially explicit analysis revealed intra-ciénega variability often masked by aggregated data, highlighting the importance of high-resolution monitoring. Seasonal and long-term trends provide context for understanding ciénega dynamics, including degradation and restoration pathways. This study emphasizes the importance of groundwater conservation and demonstrates how remote sensing supports long-term monitoring. The STM framework offers a practical tool for adaptive management to sustain freshwater resources in arid environments.