This hermeneutic phenomenological research aims to explore how Jamaican students who extend their studentship beyond four years in a Higher Educational Institution (HEI) experience academic and social integration in Jamaica. The study was guided by three research questions three sociological models and one leadership theory. Astin's (1984), Tinto's (1975), and Swail Watson's Geometric Model of Student Persistence and Achievement (1995, 2004) models and one leadership theory the Path-Goal Leadership Theory. The purposive homogeneous sampling technique was used to select 12 participants. Data were collected using a semi-structured interview schedule and were analyzed using the NVIVO 14. The findings showed that the students whose studentship extended beyond four years had failed modules, additionally, had academic and social challenges, lacked a sense of belongingness, and were supported by peers, friends, and faculty support, which had implications for socio-academic integration. Recommendations were made on how Academic Leaders could implement strategies and policies to improve socio-academic integration and consequently improve the rate of on-time graduation in HEIs. [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.]