In this study we seek to better understand the outcomes of online education by observing the role of learners' personality traits. Under the premise that the behaviors that maximize learning are contingent on the delivery method, we compared learning outcomes of students participating in four sections of an undergraduate principles of management course--three sections were taught using the online approach and one section was taught using the classroom teaching approach (N = 132). Following a multi-group quasi-experimental design, we controlled for differences in teaching delivery styles between the online and traditional classes. Then, we utilized students' personalities as the key independent variable of learning across classes. Our results corroborate that personality is an independent variable worthy of consideration in online settings. Results also suggest that future research in these settings benefits from considering narrow descriptions of personality as opposed to traditional broad traits (e.g., the big-five model). Specifically, we argue that online education demands a particular set of behavioral patterns (i.e., low gregariousness, achievement orientation) necessary to navigate the idiosyncrasies of online education (e.g., social isolation, schedule flexibility). We discuss the theoretical implications of our results in the context of online education and offer practical suggestions for online teaching design.