Entrepreneurship education and training are an increasingly widespread component of governmental and nongovernmental efforts to address the interrelated challenges of youth unemployment and poverty reduction. In the absence of consensus regarding how best to design learning opportunities that effectively prepare youth to improve their livelihoods, this chapter explores the central debates surrounding three components that are integrated into most entrepreneurship training initiatives: learning, earning, and saving. Drawing on existing literature and considering three entrepreneurship training programs underway in East Africa, the authors argue that the effectiveness of any particular youth entrepreneurship program is highly dependent on a variety of contextual considerations, many of which are beyond the control of individual youth and program managers. Implications of this are that (a) program managers need to be modest in their expectations of program effects and avoid overpromising, (b) training is needed to help prepare youth to recognize, understand, and cope with various contextual factors that impact their livelihoods, and (c) NGOs and other private organizations that implement such programs are in a position to address certain contextual factors. By highlighting key debates relevant to the design of entrepreneurship training programs, this chapter contributes to the development of entrepreneurship training initiatives that are responsive to contextual realities, thereby increasing the potential effectiveness of entrepreneurship training as a poverty alleviation strategy.