Background/Question/Methods: Huasteca-Sur is the northernmost extension of tropical forests in the American continent and home to a large indigenous population. Despite recurring crises in orange, coffee and sugar-cane markets associated with neoliberal politics, the life-support systems of many small-holder communities in this mountainous region are still based on these cash-crops. However, unstable climatic, economic, and social conditions over the past 50 years have invoked repeated transformations in land use. What were the principal drivers for land-use change leading to particular livelihoods? To address this question, we conducted a study in a small watershed in Huasteca-Sur, Mexico examining 1) key socioeconomic and biophysical variables that explain the development of land-use history and livelihoods, 2) thresholds for change and 3) key cross-scale interactions/feedbacks responsible for local adaptations and/or transformations. As an integrative framework of analysis, we applied the Dryland Development Paradigm, which considers simultaneously the biophysical and socioeconomic dimensions of land degradation. We conducted detailed interviews with farmers, compared temporal land cover/use change (with aerial photos from 1976, 1996, 2006) and analyzed emerging livelihoods of an increasing rural population in a geographically/environmentally confined space. Results/Conclusions: Over the past 50 years, farmers have adopted new land-use types coupled with new livelihoods in response to a changing demand in agricultural products, strong fluctuations in crop prices, crop-damaging freezing events, restrictive land heritage policies and emerging possibilities for alternative income through migration. All these drivers have contributed to pronounced spatiotemporal dynamics in land use/cover in this region. Applying multivariate analyses, we identified three distinct livelihoods shaping this landscape: two groups of elder-generation typical “farming-oriented” livelihoods diversifying production with a) citrus fruit, sugar-cane and maize, or only b) sugar-cane and maize, and c) a younger-generation “proletarianized” livelihood, which mainly specializes in producing - with less local work - lower quality citrus fruit for juice factories,  combined with seasonal national or international wage labor. Under multi-factor crises, two competing adaptation strategies have emerged: specialization in a single crop and simultaneous access to salaried jobs, and diversification of land use. These practices have led to highly fragmented landscape, where crop simplification is causing severe degradation of fundamental supporting ecosystem services. We propose to explore participative adaptive land-use options both to meet the needs of farmers and to allow the conservation of fundamental ecosystem services, on which potential newly evolving livelihoods may depend. These land-use/management options should be resilient to changing climate conditions, economic surprises, and increasing human population growth.