Increasingly, a number of information and communication technology (ICT) initiatives have been deployed at all levels of the education system in Jamaica in an effort to enhance and support the development of Jamaican students. An assessment of the impact of these initiatives is key in defining the way forward for the role of ICTs in education. In this paper, we explore insights from early observations from the planning and implementation of a One-Laptop-per-Child (OLPC) project at the early childhood and primary levels in two Jamaican schools.