Silvopastoral systems combine wood perennials with forage and livestock. These multipurpose wood-pasture habitats represent an important part of European bio-cultural and ecological heritage. However, their gradual disappearance due to processes of farm abandonment and intensification as well as forestry abandonment threatens biodiversity conservation and bio-cultural heritages. The behaviours of forest owners and livestock farmers determine the success of silvopastoral systems since a productive coherence between forest management and livestock grazing is required for their optimal functioning. In this study, we investigate the livestock farmers’ and forest owners’ attitudes and opinions towards wood pasture grazing and their relationship with structural factors and farming objectives in two Spanish regions. We used data collected through surveys to identify opportunities, synergies, and barriers in the integration of these actors in joint silvopastoralism. The results reveal a relationship between production objectives and positive attitudes towards silvopastoralism and the environmental functions provided by this activity, in both farmers and forest owners. Cattle farmers express a greater economic interest in wood pastures, as compared to sheep farmers who perceive more difficulties in using them. Acknowledgement of the role of grazing in landscape maintenance is positively correlated with a wide spectrum of objectives of forest owners, from the economic-productivist to the more altruistic profiles. The most synergies are found between cattle farmers and small forest owners for joint silvopastoral management. However, the incorporation of sheep grazing is advisable for the sustainable management of these systems, and hence additional efforts may be required to integrate such farming systems into silvopastoral management. As it currently stands, the EU Common Agricultural Policy appears to be inadequate for maintaining silvopastoral systems.