In a context of global agricultural intensification, integrating conservation and agricultural production is a major challenge. We have tackled the problem using a transdisciplinary research framework. Our work focuses on part of the upper Lachlan River catchment in southeastern Australia. The region is dominated by livestock grazing, and is part of an internationally recognised threatened ecoregion because most native woodland vegetation has been cleared. In productive areas, most remnant vegetation occurs as scattered and isolated paddock trees, which are dying from old age and not regenerating due to agricultural practices. The policy context and industry trends present additional risks for sparse trees. These declining trees provide many ecosystem services, including enhanced water infiltration, shade for livestock, aesthetic and cultural values, and habitat for native species. Our research aims to identify management options and policy settings that enable landscape-scale tree regeneration while maintaining grazing production. Our findings highlight tensions between the trajectory of tree cover in the region and stakeholder values. Under status quo management, many scattered and isolated paddock trees will be lost from farms, although most farmers would like to see them persist. Case studies on selected farms reveal management strategies that may be more sustainable in terms of tree regeneration and agricultural productivity, such as rotational grazing. In addition to these applied insights, our work provides a case study illustrating how a transdisciplinary study can be conducted efficiently by a small team. Our pragmatic approach has successfully combined targeted disciplinary activities with strategic collaborations and stakeholder engagement, all united by shared landscape, case graziers, and outreach activities.