This paper attempts to identify the major factors associated with some of the failures and successes of integrated watershed management policies and projects with a particular emphasis on the uplands of mainland Southeast Asia. It argues that many policy measures have been misguided by failing to acknowledge the multidimensional facets of sustainable watershed management and putting too much emphasis on command-and-control approaches to resource management and onesize-fits-all conservation models. Attempts to introduce soil and water conservation measures, for instance, have largely failed because they concentrated merely on the technical feasibility and potential ecological effects, while neglecting economic viability and socio-cultural acceptance. The production of agricultural commodities, on the other hand, has mostly been market-driven and often induced boom and bust cycles that compromised the ecological and social dimensions of sustainability. Purely community-based approaches to watershed management, on their part, have often failed to address issues of elite capture and competing interests within and between heterogeneous uplands communities. Drawing on a review of recent experience and on lessons from initiatives in a long-term collaborative research program in Thailand (The Uplands Program) aimed at bridging the various dimensions of sustainability in the Southeast Asian uplands, this paper discusses how a socially, institutionally and ecologically sustainable mix of agricultural production, ecosystem services and rural livelihood opportunities can be achieved through incentive-based policies and multi-stakeholder partnerships that attempt to overcome the (perceived) antagonism between conservation and development in upland watersheds of Southeast Asia.