Private forests in the southeastern US are critical for providing a variety of ecosystem services, including timber production and water resource protection. Restoration of longleaf pine (LLP) forests and savannas tends to enhance some ecosystem services, including water supply, over timber production. A variety of payments for watershed services (PWS) strategies have emerged to address the market failure associated with private forests and public water supply. The nature of these programs suggests that biodiversity protection may be a positive externality, or third-party benefit, to water resource protection. This paper uses a critically engaged research approach and expert interviews to investigate how PWS programs may help prevent land use change and promote LLP restoration. We also offer recommendations on how to sustain emerging efforts to implement PWS strategies while including LLP restoration objectives.