This mixed-methods study examined the effectiveness of the Upward Bound TRIO program in preparing a low-income and first-generation population for the successful completion of high school and acceptance into postsecondary institutions of higher learning. Data collection methods for this study were comprised of teacher and student surveys and program director interviews. A comparison of two Upward Bound programs was conducted in the southern regions of Virginia and Georgia. The results were analyzed and queried as to whether the current program objectives were effective in meeting the needs of low-income, first-generation students and whether the program provided the necessary academic and technological skillsets and support needed to gain employment in knowledge capital economy. The goal of Upward Bound is to increase the rate at which participants complete secondary education and enroll in institutions of higher learning. The significance of this study is that it offers insight on the necessary support structures needed to assist low-income and first-generation students. The study was an in depth analysis of the Upward Bound TRIO program’s current objectives in meeting the needs of the 21st century learner. Information gathered from the literary sources as well as other sources provides additional insight for the researcher on program practice, evaluation, efficiency, and low-income first-generation students’ success.