Government and development organizations are increasingly turning to entrepreneurship training programmes as a means of assisting those caught in poverty to develop the skills needed to find or create employment. Drawing on case studies from East Africa, this article argues that while such programmes offer a potentially useful strategy for enabling youth to access and create employment opportunities, they are, in and of themselves, an insufficient strategy for sustained improvement in the livelihood of participants. The article presents a model of contextual factors that it argues have broader applicability and relevance than the models currently in wide use. Without sufficient attention to those factors, the shift toward entrepreneurship training as an approach to poverty alleviation may place undue burdens and unachievable expectations on the very youth such programmes are designed to support.