Studies show that increased access to education can contribute to economic growth and poverty eradication, accordingly, acquired basic skills such as reading, writing and numeracy have a positive effect on marginalized populations’ incomes and the rate of return on the economy. The wish to eliminate poverty in Kenya has been articulated since independence through a number of enactments and policy papers. However rampant poverty still abounds. Abject poverty threatens access to essential services by about 38% of Kenyans living below the poverty line. In its effort to combat poverty, the government introduced free primary and free day secondary education with poverty alleviation as one of its objectives. However, the free basic education has so far not eliminated poverty as envisaged due to a number of challenges. This paper thus presents the successes, failures and challenges of the free basic education in Kenya against the need for it to help eliminate poverty by thematically examining and analysing literature. From the analysis, the successes include: increased school enrolment, reduction in illiteracy levels, improved transition rates to secondary school, eradication of child labour, improved assessment and placement of learners with disabilities and abandonment of harmful traditional practices. The challenges include: understaffing, massive unplanned expansions of schools, inability of parents to provide subsistence, the quality issue and delayed funds disbursement amongst others, thereby rendering education unable to efficiently play its role in poverty alleviation. Recommendations are thereafter given