Seminatural European grasslands and pastures have a high conservation value because they provide different goods and services (meat, wool, carbon sequestration, etc.) and harbor diverse communities of plants and animals. These land use systems were created by low- and moderate-intensity use and, nowadays, face threats from both abandonment and overuse. Although less productive or less accessible areas are abandoned, triggering afforestation processes, others are subject to intensive agricultural practices with the addition of production factors and modern management schemes. Neither is comparable with the traditional uses that first formed and maintained these systems for generations, and therefore, it is fundamental to design effective policies to ensure a sustainable territorial coexistence of modern agriculture and traditional pastures and grasslands. In this work, we assessed the recent dynamics of pastures and grasslands in Slovenia. The results show distinct local changes and a nationwide general dynamic of area reduction and loss of patches. After elaborating on how such changes affect the landscape and some species according to their traits, we provide practical recommendations for policy design to contribute to protecting and promoting this land use system. We argue that the two major priorities should be to preserve the most relevant patches and to try to convert other land uses into grasslands, preferably attempting to merge separated patches and thus increasing the mean patch size of grasslands. Overall, by identifying trends, locating the different spatial changes, and complementing with a connectivity analysis, this approach can be valuable in identifying effective measures to protect and improve grasslands. Besides the concrete results obtained from the Slovenian case study, the underlying rationale and work-flow can be applied elsewhere to produce similar outputs that help identify land transformation patterns and interpret specific land use category dynamics.