Increasing demand for agricultural products is driving grassland management intensification with subsequent impacts on ecosystem services and disservices. Key questions related to grassland production as well as environmental and social concerns must be addressed to ensure sustainability. We propose a unified perspective, addressing numerous trade-offs and synergies between grassland ecosystem services and disservices, and considering an array of ecological and human consequences associated with history and ongoing shifts in management strategies. Much of our discussion utilizes evidence from humid grasslands; however, our examples and recommendations have global implications for the future of grassland management. We characterize four categories of ecosystem services and disservices (provisioning, supporting, regulating, and cultural) provided by perennial grasslands that are extensively managed (low or no input, never cultivated) or intensively managed (high-input, cultivated). We explore a range of potential outcomes following transition from extensive to intensive agroecosystems around the globe. Additionally, we suggest specific research priorities to better evaluate ecosystem services and disservices across management intensities. Finally, we highlight potential benefits of landscape mosaics that include grasslands across a continuum of extensive to intensive strategies.