The Career Advancement Programme (CAP), launched by the Jamaican Ministry of Education (MOE) in January 2010, is a major government policy initiative whose primary aim is to address the problem of inadequate preparation of school leavers for the workforce and further education. This problem was identified over 40 years ago, and a number of policy initiatives have been implemented by successive Jamaican governments to address it. However, it continues to exist. This paper is an attempt to understand the challenges faced by these policy initiatives and to discuss the implications for the CAP which is currently being implemented by the Ministry of Education. The specific policy interventions which were examined are the (a) Grades 10 and 11 Programme, (b) HEART Trust/National Training Agency (NTA), (c) Reform of Secondary Education Programme (ROSE I and II), (d) Jamaica Movement for Adult Literacy (JAMAL) now the Jamaica Foundation for Lifelong Learning (JFLL), and (e) National Youth Service (NYS). The author contends that based on the experiences and outcome of the policy initiatives implemented since 1974, the CAP will encounter serious threats unless corrective measures are taken to minimize the impact of these deficiencies, including structural changes to the non-formal education system.