Silvopastoral systems are traditional components of the landscape in the Swiss Jura Mountains, and are promising approaches for the sustainable management of mountain areas worldwide. Due to complex vegetation dynamics, pasture-woodlands are very vulnerable to the currently occurring land use and climate changes. Therefore, management requires integrative long-term predictions of successional trends. We present a refined version of the spatially explicit, dynamic simulation model WoodPaM with improved climate sensitivity of simulated vegetation. We investigate pasture-woodland dynamics by applying an innovative combination of retrospective simulations starting in the Middle Ages with prospective simulations following two climate change scenarios. The retrospective simulations demonstrate the strong dependency of the landscape mosaic on both climate and management. In high elevation mountain pastures, climate cooling during the Little Ice Age hindered simulated tree regeneration and reduced forage production of grasslands. Both led to an increase in open grassland and to a structural simplification of the landscape. In turn, climate warming afterwards showed the opposite effect. At lower elevations, high cattle stocking rates generally dominate simulated succession, leading to a slow development of quite homogenous landscapes whose structures are hardly affected by historical climate variability. Aerial photographs suggest that logging and windstorms critically shaped the current landscape, both homogenizing mosaic structures that emerge from selective grazing. Simulations of climate change scenarios suggest delayed but inevitable structural changes in the landscape mosaic and a temporary breakdown of the ecosystem service wood production. The population of currently dominating Norway spruce collapses due to simulated drought. Spruce is only slowly replaced either by beech under moderate warming or by Scots pine under extreme warming. In general, the shift in tree species dominance results in landscapes of less structural richness than today. In order to maintain the mosaic structure of pasture-woodlands, we recommend a future increase in cattle stocking on mountain pastures. The (re-) introduction of mixed herds (cattle with horses, sheep, and goats) could mitigate the simulated trend towards structural homogenization of the forest-grassland mosaic because diverse browsing effects selectively control tree regeneration and would counteract simulated forest encroachment. This could prevent the loss of species-rich open grasslands and forest-grassland ecotones. Forest management should respect forest-grassland mosaics and ecotones by following the traditional selective felling of single trees instead of large clear-cutting. Additionally, beech regeneration should be promoted from now on in order to smoothen tree species replacement with warming and to ensure the continuous provision of forest ecosystem services.