An effective implementation of payment for environmental services (PES) must allow for complex interactions of coupled social-ecological systems. We present an integrative study of the pasture-woodland landscape of the Swiss Jura Mountains combining methods from natural and social sciences to explore feedback between vegetation dynamics on paddock level, farm-based decision making, and policy decisions on the national political level. Our modeling results show that concomitant climatic and socioeconomic changes advance the loss of open grassland in silvopastoral landscapes. This would, in the longer term, deteriorate the historical wooded pastures in the region, which fulfill important functions for biodiversity and are widely considered as landscapes that deserve protection. Payment for environmental services could counteract this development while respecting historical land-use and ecological boundary conditions. The assessed policy feedback process reveals that current policy processes may hinder the implementation of PES, even though a payment for the upkeep of wooded pasture would generally enjoy the backing of the relevant policy network. To effectively support the upkeep of the wooded pastures in the Jura, concomitant policy changes, such as market deregulation, must also be taken into account.