This qualitative descriptive study explored the college preparatory experiences of African American male students who participated in a Northwest Louisiana TRiO Upward Bound program before college enrollment. Specifically, the students in this study perceived that TRiO Upward Bound programming influenced their college readiness and enrollment. The perception of TRiO Upward Bound enhanced the student's college readiness and enrollment with increased college preparatory services while in high school. This study responded to the following research questions: (a) How do African American men describe their participation experience in the TRiO Upward Bound program? and (b) How do African American men describe the role of TRiO Upward Bound as a contributor to their college readiness and enrollment? The participants for this study were ten African American males currently enrolled in a postsecondary institution. Data were collected through semi-structured interviews. The data collected for this study provided additional insight regarding participant experiences as perceived by African American males. The findings of this study sought to display the connection between TRiO Upward Bound's college preparatory programming to modern-day college readiness. The analysis of the data yielded six major themes (a) Academic Performance, (b) Co-Curricular Experience, (c) Standardized Test Preparation, (d) Collegiate Exposure and Exploration, (e) Noncognitive Mastery, and (f) Rigorous Secondary Program of Study. The information gleaned from this study may contribute to the scarce body of knowledge regarding the college preparedness of African American males. [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://www.proquest.com/en-US/products/dissertations/individuals.shtml.]