Demand-side financing interventions such as scholarship programs are promising to be viable financing strategies of reaching out to the poor and marginalized children in order for them to access basic education. Although such financing strategies have been praised as successful in mostly Latin American countries, very little is systematically known about how this would work in poor African countries such as Malawi. This study therefore examines demand-side financing strategy through an evaluation of a scholarship program implemented in Malawi.It uses qualitative mode of inquiry through in-depth interviews of 36 key participants as a primary method of data collection.In addition, it reviews program documents and conducts cohort analysis of some beneficiaries of the program. Findings are mixed, where on one hand success stories are registered and on the other hand, critical challenges are identified putting assumptions of such programs under a microscope.The study intends to inform policy makers and educational practitioners to critically re-examine such financing strategies in-order to design better programs for poor and marginalized children.