Past research suggests that the use of an online learning orientation is an effective proactive strategy to ease online students' transition into online learning. Based on a sample of 3,888 online students from an urban public university, we used ordinal logistic regression to understand the influence of students' satisfaction with an online learning orientation (OLO), their prior level of online learning experience, and their demographics on their academic self-efficacy (ASE). Consistent with prior research, our findings confirmed the influence of students' satisfaction with OLO, their prior online learning experience, and their gender on their ASE. Unsatisfied students were 85% less likely than satisfied students to express a high level of self-efficacy. In contrast, students' age and enrollment status proved not to be significant. Overall, our findings provide strong evidence about how the use of an OLO as proactive support strategy can boost online students' academic self-efficacy.