Conservation and policy agendas, such as the European Biodiversity strategy, Aichi biodiversity (target 5) and Common Agriculture Policy (CAP), are overlooking the progress made in mountain grassland cover conservation by 2020, which has significant socio-ecological implications to Europe. However, because the existing data near 2020 is scarce, the shifting character of mountain grasslands remains poorly characterized, and even less is known about the conservation outcomes because of different governance regimes and map uncertainty. Our study used Landsat satellite imagery over a transboundary mountain region in the northwestern Iberian Peninsula (Peneda-Gerês) to shed light on these aspects. Supervised classifications with a multiple classifier ensemble approach (MCE) were performed, with post classification comparison of maps established and bias-corrected to identify the trajectory in grassland cover, including protected and unprotected governance regimes. By analysing class-allocation (Shannon entropy), creating 95% confidence intervals for the area estimates, and evaluating the class-allocation thematic accuracy relationship, we characterized uncertainty in the findings. The bias-corrected estimates suggest that the positive progress claimed internationally by 2020 was not achieved. Our null hypothesis to declare a positive progress (at least equality in the proportion of grassland cover of 2019 and 2002) was rejected (X2 = 1972.1, df = 1, p < 0.001). The majority of grassland cover remained stable (67.1 ± 10.1 relative to 2002), but loss (−32.8 ± 7.1% relative to 2002 grasslands cover) overcame gain areas (+11.4 ± 6.6%), indicating net loss as the prevailing pattern over the transboundary study area (−21.4%). This feature prevailed at all extents of analysis (lowlands, −22.9%; mountains, −17.9%; mountains protected, −14.4%; mountains unprotected, −19.7%). The results also evidenced that mountain protected governance regimes experienced a lower decline in grassland extent compared to unprotected. Shannon entropy values were also significantly lower in correctly classified validation sites (z = −5.69, p = 0.0001, n = 708) suggesting a relationship between the quality of pixel assignment and thematic accuracy. We therefore encourage a post-2020 conservation and policy action to safeguard mountain grasslands by enhancing the role of protected governance regimes. To reduce uncertainty, grassland gain mapping requires additional remote sensing research to find the most adequate spatial and temporal data resolution to retrieve this process.