Information and Communication Technology for Development (ICT4D) initiatives are of critical significance in addressing socio-economic development challenges in the developing world. Within the wide ICT4D theme, education is a central sector to develop human capital, provide universal access to knowledge, and enable people with knowledge and skills for an evolving global economy. This paper provides a critical evaluation of ICT4D solutions for education in the developing world. Taking a qualitative case study perspective, it examines the One Laptop Per Child (OLPC) and Kenya's Digital Learning Program (DLP) with a view to deriving valuable lessons. The conclusions emphasize the point that successful integration of ICT calls for an integrated, context-oriented approach to infrastructure, teacher professional development, suitable content, sound financing, and strong political will.