For many open-enrolled higher education institutions, including community colleges, enrollment is dropping each semester creating significant financial challenges. While much research literature focuses on four-year colleges, little is known about the students who seek to enroll at community colleges. What is known is often evaluated using college choice theoretical models, e.g., Hossler & Gallagher (1987), that focus on a limited, and often linear, student experience. Contemporary evaluation models, including Perna (2006) and Iloh (2018), seek to expand college choice understanding by incorporating contextual matters that include the diverse experiences of potential students as they consider college. These contextual theories, with parallels to leadership literature, are used to inform and motivate this study in seeking to identify factors that may improve enrollment. Utilizing application and FAFSA data from potential students who applied to a mid-sized community college in Virginia, the study uses logistic regression to consider the primary research question of whether students will enroll or not. By incorporating demographic, academic, socioeconomic, and family variables, five theoretically driven models were developed and analyzed to answer the research question. Results from these models indicate that gender, age, expected family contribution, student earnings, dependency status, and selected categories of race, academic goals, and admit types were statistically significant in predicting enrollment holding other variables constant. These findings provide insight regarding the decision-making of students at one open-enrolled community college with application and recommendations for enrollment managers, institutional leaders, and higher education practitioners. [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.]