This chapter examines the evolving trajectory and emerging lessons from twenty years of agroforestry project activities in Haiti that made it possible for more than 300 000 Haitian peasant households – over a third of the entire rural population of Haiti – to plant wood trees as a domesticated, income-generating crop on their holdings. Unusual popular enthusiasm for the project derived from several anthropological and technical design factors: the adaptation of the project to pre-existing Haitian land tenure, tree tenure, and market systems; the elevation of micro-economic over macro-ecological themes; the decision to bypass the Haitian government and operate the project through local NGOs (non-government organizations); the use of a joint-venture mode in which smallholders supplied land and labor and the project supplied capital in the form of seedlings; the use of professionally managed small-container seedling technology rather than backyard nurseries; and a project management policy that encouraged farmer-induced deviationsfrom project assumptions in matters of tree deployment and harvesting schedules. Issues of secure tree tenure were central to farmer planting decisions. The article discusses how secure tree tenure was possible under the heterogeneous informal arrangements that characterize Haitian peasant land tenure. The approach generated the birth of several creative Haitian peasant agroforestry configurations described in the chapter. In discussing lessons learned, the authors argue that long-term environmental payoffs should be viewed, not as the principal project goal, but as secondary side effects of smallholder tree planting decisions made for short-term micro-economic reasons.