This intrinsic case study investigated the experiences of select low-income and first-generation students who participated in the Upward Bound program throughout high school to understand how participation influenced enrollment at a postsecondary institution. Two theoretical frameworks guided this research study: Astin's (1984) I-E-O model and Kolb's (1984) experiential learning theory. Six participants were recruited to participate. Individual semi-structured virtual interviews were conducted and completed for data used in this study. Castillo-Montoya's (2016) Interview Protocol Refinement (IPR) framework was referenced to generate interview questions. Multiple forms of analyses (i.e., constant comparison analysis and discourse analysis) were used to strengthen the credibility of this study. Findings were presented through emerging themes, which were generated from unique language segments provided by participants. These themes highlighted the unique experiences of Upward Bound students and how participation in the program influenced their postsecondary enrollment decisions. Themes included: (a) participants' academic achievement, (b) programmatic assistance offered, (c) influential support systems, (d) postsecondary exposure, and (e) goal setting. The study results produced implications and recommendations for future research. The first implication revealed that providing college preparation resources and specialized support to low-income and first-generation students increases the probability that students will enroll in and persist with their postsecondary education. The second implication suggested that generational poverty will continue to exist among low-income and first-generation students who do not have access to critical college preparation resources. Lastly, the third implication called for the expansion of equitable and accessible resources, specifically designed for low-income and first-generation college students. Recommendations for higher education included a demand for policymakers and educational administrators to advocate for increased funding of Upward Bound to expand resources. Practitioners would benefit in conducting additional research that targets those Upward Bound alumni who did not pursue a college education to determine deficits. Recommendations for future research include evaluating college preparation efforts conducted by high school teachers and counselors. Upward Bound practitioners should evaluate their partnership with the school districts they serve to improve a collaborative approach to college readiness for all students. [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.]