Demand for arable farmland is growing globally. The need for land-based products, such as food, feed, biofuels, and timber, as well as conservation efforts to preserve biodiversity and create carbon sinks, is driving intense competition over finite land resources. A key challenge facing humanity is how land can be allocated efficiently to these purposes while also feeding an increasing worldwide population and bolstering global food security. While agricultural production alone cannot guarantee food security, land use decision-making is becoming increasingly critical to establishing pathways towards food security in developing contexts. This dissertation uses Ethiopia as a case study to explore how international development policies designed to work in any geographical and institutional country context can backfire if local institutional, ecological, and socio-economic factors are not taken into consideration in the policy’s design. First, I examine the historical policy development of Ethiopia’s land rights and tenure system. Using qualitative process-tracing and path dependency analysis, I identify the key causal dynamics and critical junctures that entrenched Ethiopia’s nationalized land tenure system over time. In doing so, I set the stage for the remainder of the dissertation, which explores how and why certain development instruments—specifically, contract farming schemes—that have produced positive results in other regions of sub-Saharan Africa, ultimately failed in Ethiopia. Second, I investigate how a contract farming intervention in Ethiopia’s Awash River Basin changed smallholder farmers’ crop cultivation choices and patterns from 2005-2015. Using a time series of five single-date satellite images over the course of the period in question, land use change vectors are derived for each smallholder parcel to determine the effect of the contract farming scheme’s introduction on crop choice for those participating farmers. Based on a series of covariate measures, a neighboring district was selected to serve as a control group. Following spatial analysis, a difference-in-differences econometric test was undertaken to determine the effect of treatment on the treated. Ultimately, I find that the introduction of the contract farming scheme causally influenced participating smallholder farmers to switch from growing subsistence-based crops to commercial sugarcane. Third, and finally, I assess how household income and food security changed for those farmers that participated in the contract farming scheme at the Wonji-Shoa sugarcane factory in the Awash River Basin. In order to assess food security, I introduce a new method of measuring household food security: income-based food baskets based on local, customary diets and commodity prices. Then, using genetic matching to pair observations in the treatment and control groups, I run two Ordinary Least Squares tests for two observation periods to assess how income and food security changed post-intervention. Results from the statistical tests show that households that participated in the scheme experienced a 17-24% reduction in food security after exclusively growing commercial sugarcane for the Wonji-Shoa outgrower scheme. This dissertation concludes by offering practical changes that could be made to outgrower schemes in Ethiopia to help them function within the existing land rights and tenure system and work to achieve better food security and poverty alleviation for the country’s smallholder farmers.