Research in correctional education has focused on examining outcomes for participants and identifying principles and guidelines that reflect best practice. Relatively few studies have focused on postsecondary education programs and fewer still have sought to relate program implementation to student outcomes to inform program design and improve program delivery. This study builds on research that identifies factors associated with student success in undergraduate education outside of prison settings. Hierarchical linear models are used to examine variation in student outcomes within and between prisons and to examine the influence of student characteristics, instructional program characteristics, and institution characteristics on student outcomes. Findings are based on student assessment and survey data collected over a 2-year period as part of a national study of the Correctional Education Association College of the Air (CEA/COA) program. Results identify characteristics of students, instructional programs, and institutions that influence student outcomes and factors that moderate these relationships. (Contains 2 footnotes and 8 exhibits.)