Despite their multiple ecological benefits, semi-natural grasslands are threatened by intensification and conversion to cropland farming practices. Previous agri-environmental schemes have yet to prove successful in giving adequate incentives to farmers to engage in their restoration on a large scale. Through a discrete choice experiment conducted with 110 farmers in northwestern France, we show that participation in grassland restoration can be enhanced by introducing a conditional monetary premium contingent upon compliance with the enrolled farmland’s scope and spatial distribution conditions. We have also found that although farmers clearly prefer to avoid signing a grassland restoration contract, technical support is a significant contract attribute. Besides, our findings underline that small dairy farmers who seem knowledgeable about ecosystem services provided by grasslands prefer signing a collective contract that engages them with their neighbors toward achieving significant ecological outcomes of grassland restoration. We conclude with policy implications within the post-2023 CAP as well as a research perspective to improve the implementation of large-scale grassland ecological restoration measures.