South Africa participated in all three of the Second International Technology in Education Study (SITES). In the first international study, South Africa was the only developing country, and therefore, stark contrasts were found in the international study between South Africa and the other participating countries. Chile participated in the SITES 2006 as one of a few developing countries making the comparison with South Africa possible. Despite similarities in their contexts and economies, their approach to information and communication technologies (ICTs) in education appears to differ. This difference raised questions about differences in policies and their implementation at school level. This research conducted in South Africa found that the Chilean strategy for developing and implementing their ICT in education appear to be very different with regard to its design, the organization, the strategies adopted, the resources used and, most importantly, their approach to teacher development for implementing ICT. A number of lessons are revealed for the South African policymakers and others from similar developing contexts. (Contains 1 box, 4 tables, and 6 figures.)