The increase in the number of years of school within the Jamaican school system has caused the government of Jamaica to introduce the Six Form Pathway program. The program was introduced as an intervention method for students to stay in school longer in order to acquire the requisite subject or experience to attend university or to be employable. This qualitative research study explores opportunities and challenges faced by the six form program in Jamaican schools. The researchers interviewed five education officers and five principals from different high schools across Jamaica. The questions aimed to identify factors that high school principal and teachers might find helpful as students matriculate to university and world of work. The study produced four significant themes that affect students' funding, qualification of students, transition to higher education or the workforce and teaching methods. The study's implications and recommendations can help stakeholders engage in activities that aid in students' successful matriculation from high school to university and to contribute more to the world of work. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://bibliotheek.ehb.be:2222/en-US/products/dissertations/individuals.shtml.]