Livelihood challenges such as low income, food insecurity, and poverty are prevalent among farming and rural communities in sub-Saharan Africa (SSA) and are linked to low agricultural productivity. Boosting agricultural productivity is considered pivotal to improving the livelihood conditions of farming and rural communities in SSA. Some non-governmental stakeholders and international development agencies promote organic agriculture as a pro-poor strategy to help enhance agricultural productivity and farmers’ livelihoods conditions in SSA. For reasons yet to be well-understood, the adoption rates of organic farming by smallholder farmers in SSA is low. To fill these gaps, in four essays, this dissertation investigated the barriers and the factors that influence and gender the adoption of first-party certified organic leafy vegetable production (OLVP) by smallholder farmers in Ibadan, southwestern Nigeria. The first essay developed a gender-aware and livelihood-based conceptual framework named TALAF, which was used to inform the second and third essays. The second essay qualitatively examined the factors that influence, inhibit and gender the adoption of OLVP. The third essay investigated the factors and contexts that motivated disadoption of OLVP in the study areas in order to generate insights about what can be done to avert or stem the phenomenon. The fourth essay combined participatory causal loop diagraming with network analysis to map and contrast the similarities and differences in the causal mechanisms that dynamically interact to affect the adoption of organic farming in urban and rural Nigeria. As a whole, the dissertation contributes to the literature on the adoption, disadoption and gendering of organic farming in Nigeria and Africa. Through TALAF, the dissertation offers a conceptual framework which can help untie the complexity in technology adoption decision-making.