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. This study assesses some of the critical enablers and success factors of the programme involving the supporting interaction and participation of students, teachers, parents, and the wider community. The findings reflect the benefits of the project for all stakeholders, and provide a platform on which to build for future project implementations in Jamaica and the Caribbean.