Public institutions of higher education have a dual mandate to provide the best possible education while also maintaining accessibility to students within its state. This study explores the knowledge, motivation, and organizational influences associated with the retention of Pell-eligible, academically at-risk freshmen, and examines an academic coaching intervention addressing this population. As a population defined by a specific performance outcome, academic probation, the causes and factors contributing to that outcome are many and varied. In an effort to provide a framework for understanding those causes and factors, this study reviews the current literature on the subject and lays out two main premises. The first being that a number of pre-existing social factors, largely stemming from structural economic inequality, increase the likelihood of becoming academically at-risk. The second being that certain active behavioral decisions on students' parts, based on pre-college levels of cultural (academic) capital, lead to a decreased likelihood of persisting to sophomore year. Taken together, the research provides a foundation for institutions to begin examining their Pell-eligible student populations and tailoring interventions in an effort to improve persistence among Pell-eligible, at-risk freshmen populations. [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.]