This study examines how technological and relational factors independently and interactively predict the perceived learning success of doctoral students enrolled in online-based leadership programs offered in the United States. The 73-item Online Learning Success Scale (OLSS) was constructed, based on existing instruments, and administered online to collect self-reported data on three primary variables: student learning success (SLS), relational factors (RF), and technological factors (TF). The SLS variable focuses on the gain of knowledge and skills, persistence, and self-efficacy; the RF on the student-student relationship, the student-faculty relationship, and the student-non-teaching staff relationship; and the TF on the ease of use, flexibility, and usefulness. In total, 210 student responses from 26 online-based leadership doctoral programs in the United States were used in the final analysis. The results demonstrate that RF and TF separately and together predict SLS. A multiple regression analysis indicates that, while all dimensions of TF and RF are significant predictors of SLS, the strongest predictor of SLS is the student-faculty relationship. This study suggests that building relationships with faculty and peers is critical to leadership doctoral students' learning success, even in online-based programs that offer effective technological support.