The purpose of this study was to investigate the influence of orientation programs on student academic and social learning. Moving beyond previous studies, we examined how participation in orientation programming affected student learning and how the impact of these programs on learning varied by organizational characteristics (i.e., institutional control, size of undergraduate enrollment, sponsoring division, and whether the institution has an office designated for managing orientation programs), student entry characteristics (i.e., gender, race, transfer status), and student experiences (i.e., perceived quality of orientation program in helping student transition and in meeting students' expectations, positive experiences with orientation staff, and perceptions of orientation programs and their efficacy in helping students navigate resources and in providing useful campus-based information). Hierarchical linear analysis was used to analyze these cross-level effects. Results demonstrated that having a designated office for orientation programs on campus was important for narrowing the academic learning gap between new-first year and transfer students. Implications for researchers and practitioners were discussed.