The present study compares the educational attainment level among the youth in two Sub-Saharan African countries, namely; the Democratic Republic of the Congo (DRC) and Madagascar, with their status in work. The study employed data from the school-to-work transition survey of the International Labour Office, 2015. This study reveals that in the two countries investigated, that youths face several challenges when negotiating their move to employment because the educational attainment of the majority of them is deplorable. Financial burdens and exam failures are the critical reasons why the youth of these two countries leave school early and engage in low-quality jobs to secure their living. Besides, young wage workers are most likely to be exposed to exploitation, since their employment is usually based on an oral contract.