In the Philippines, over 25 million people live in upland areas, relying heavily on farming. These uplands, largely forest land, fall under the Department of Environment and Natural Resources (DENR), creating complex and conflicting land-use regulations. Insecure land tenure discourages investment in long-term practices like tree planting and contributes to deforestation, which in turn causes erosion, water scarcity, and income loss. This study investigates agroforestry systems in the Philippine uplands as a sustainable land-use strategy—defined as one that conserves the environment while supporting farmer livelihoods. The Model for Assessing the Sustainability of Agroforestry Systems (MASAS) was used in Southern Leyte and Claveria to evaluate 100 agroforestry parcels across six crop-based strata. Timber tree systems scored highest in sustainability, while coconut and banana systems scored lowest. Timber, rubber, and coffee systems performed best environmentally; rubber and timber also led socio-economically. Proper transition management, training, and access to quality inputs were key success factors. No trade-off was found between environmental and economic outcomes. Secure land tenure correlated with higher income and greater willingness to plant trees. The study recommends capacity building, better access to seedlings and inputs, support for nurseries, streamlined tenure processes, and improved market access. Challenges in timber marketing and DENR permit acquisition hinder farmer motivation. Effective promotion of agroforestry requires addressing these legal and market barriers. Further research is recommended on transition management, carbon storage, and biodiversity in agroforestry