A quasi-experimental investigation assessed the impact of multiple factors, including financial aid and proactive advising, on retention of undergraduate students at a small, private university that primarily serves online learners. In-house proactive advising over three academic years was positively associated with increased retention semester-to-semester and fall-to-fall. In addition, students who received Pell Grants plus at least one other form of financial aid, completed math remediation, and transferred 30 or more credit hours persisted at higher rates semester-to-semester. Individuals identifying with historically underrepresented groups tended to persist at rates lower than their White peers’ semester-to-semester retention. These findings support the efficacy of proactive advising and financial aid, even with a population that exhibits lower retention for persons from historically underrepresented groups. Findings also suggest that students who transfer more than two full-time semesters of credit have a strong motivation to complete their course of study.