This essay prompts critical thinking on the way ICT-enabled education programs in Africa have been conceptualized and implemented. It reflects mainly on the experiences of the African SchoolNet movement over the past decade. It highlights important lessons and demonstrates the beneficial effects of technology-enhanced learning programs on African learners and teachers who have had the privilege of being included in SchoolNet initiatives. However, it also shows that the accumulated interventions and programs to date remain insignificant in scale to catalyze a resounding shift toward resolving the crisis in Africa’s education systems; it makes the case for integrated system-wide, locally led approaches that soberly takes account of the challenges imposed by globalization. The chapter traces the historical evolution of frameworks to promote African inclusion in the information society, and allusions are specifically made to the emergence of the NEPAD eSchools, and the Global eSchools and Communities Initiative of the UN ICT Task Force, which hold the potential for advancing the frontiers of learning in Africa. Here, the author emphasizes, however, that these new initiatives need to draw on the accumulated learning and experience of the SchoolNet movement over the past 10 years in Africa to succeed. Finally, the chapter raises the dearth of evidence-based research made in Africa by Africans who would verify or refute the case for stronger investment in ICTs for education. It then proffers suggestions on areas for further research.