Using a post-colonial lens, this paper describes the changes and constants in Jamaica’s educational system between the 19th and the early 21st century using academic literature and secondary data from the Ministry of Education. High schools initially emerged in Jamaica for the upper and middle classes only, based on the families’ income level, thus excluding children from the lower income bracket. Over time, breaking the glass ceiling for lower-income students became more possible as education included students moving from elementary to high school based on merit. This still restricted a large body of lower-income students who needed the tools and merit for success in the exit examination to high schools. In the 21st century there is more direct intervention in the Jamaican school system through funding and policies that change the high school education structure available to lower-income families, making it more possible for upward mobility on the social ladder. While there may be legacies of the colonial era, Jamaica has made significant strides in moving away from her turbulent past.