Permanent grasslands (PG) provide multifunctional ecosystem services (ES) in Europe and globally, which are threatened by both increased farming intensity and land use change in marginal areas. Farm management decisions can represent critical thresholds, or behavioural “tipping points”, in the agricultural system. Decisions are influenced by a combination of agronomic, policy and social factors. Transformation of PG systems can be facilitated through positive tipping points and relevant policy implementation to ensure sustainable PG systems. The aim of this research was to understand the drivers of decisions regarding land use changes and management towards critical positive and negative tipping points across five biogeographic zones in Europe. Interview methodology assessed farmers’ preferences and priorities regarding the adoption of sustainable PG systems. Participants were selected from five case study countries, each representing a different biogeographic zone in Europe (Continental/Pannonian: Czech Republic, Boreal: Sweden, Mediterranean: Spain, Alpine: Switzerland, and Atlantic: UK). The sample also covered three farming intensity types within these biogeographic zones: high input/intensive conventional farms (≥1.0 LU/ha); low input/extensive conventional farms (<1.0 LU/ha); and certified organic farms. In total, 373 farm interviews were obtained from the case study countries between October 2020 and October 2021. The analysis focuses on drivers of change and considers tipping points across these countries, considering case studies of land use changes (specifically land abandonment) and land management practices (specifically changes in stocking rates). The most common reasons for PG management changes towards either intensification or extensification were economic. Farmers require policy support to increase provision of non-market ES, while rebalancing subsidies can deliver environmental ES at scale through abandonment (e.g., through the creation of specific habitats that support some threatened species). Agri-environment schemes (AES)and subsidies could be more flexible to allow farmers to better adapt grassland management to local production conditions and unpredictable circumstances such as droughts, floods, or market shocks. To maintain PG that delivers more goods and services, financial compensation for ES delivery was perceived to be the most significant support mechanism needed, while easier access to ES provision expertise through extension or consultancy services is considered important factor.