Purpose, especially in its generous form, may serve as a critical catalyst on the path to thriving for adolescents. However, while there is a growing amount of research about purpose, less of it focuses on ways in which purpose might be supported by both individual and contextual variables. Spirituality and schools are two such variables. The primary hypotheses of this study posited that both school generosity and relational spirituality would positively predict generous purpose. The secondary hypotheses of this study are better understood as exploratory. Specifically, I hypothesized that some relation would be found between school generosity and relational spirituality, but did not speculate about the exact nature of this relation. I also hypothesized that the spiritual context of the school would be associated with differences in relations among school generosity, relational spirituality and generous purpose, but did not speculate about the specific nature of those differences. In order to test these hypotheses, survey data was collected from ninth grade students (n = 253) at three high schools of varying stated spiritual contexts twice during the ninth grade year. The schools included a Catholic school, a Waldorf-methods school, and a community-centered charter school. Correlation and linear regression analysis led to the following results. School generosity among students and relational spirituality were both shown to be statistically significant, positive predictors of generous purpose in ninth grade students. In addition, school generosity and relational spirituality were also related to each other. First, school generosity was shown to predict relational spirituality. Second, when both were included in a regression equation predicting generous purpose, only relational spirituality remained a significant predictor of generous purpose. School-level results were more mixed, with only weak evidence found for the role of the spiritual context of the school. These results are interpreted in a positive youth development framework, pointing to the importance of peers and of school environments that provide a good fit for early adolescents. Implications for both PYD theory and education are discussed.