Several studies have found that higher hope is associated with higher academic achievement. Although scholars have asserted that this association is the result of higher hope leading to an increased likelihood that students will engage success-oriented behaviors (e.g., participating in class, completing homework assignments), very little empirical research has been done to test this assertion. In this study, cluster analyses yielded three clusters of hope (high, average, and low) in a high school sample (N = 447) and a college sample (N = 375). Differences among hope clusters were examined across three domains of indicators--engagement, disengagement, and motivational variables--associated with success-oriented behavior in school. Results from both samples indicated that students with higher levels of hope reported higher engagement, higher motivation, and lower disengagement, with medium to large effect sizes. These results have implications for both hope research and scaling psychosocial interventions.