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Numerous experimental studies find a positive, causal relationship between noncognitive skills (NCS) and academic achievement. However, few studies have examined how this relationship varies across school context. Using academic engagement as an illustrative case study, this paper compares the relative effect of NCS on math achievement across different levels of school wealth. My results, based on a multilevel analysis of a nationally representative cohort of ten graders in 2002, show that for three measures of achievement (test scores, rigor of coursework, and overall achievement), engagement has the strongest effect in the poorest schools and weakest in wealthy schools. These findings are consistent with frog-pond theories of education and suggest that differences in relative competition may drive this differential return on engagement across schools. From a theoretical perspective, this study extends current sociological research on engagement by illustrating the critical role of school context—in this case school wealth— in shaping the strength of its effects on achievement. From a policy perspective, they suggest that a greater focus on NCS may be a viable approach in helping narrow persistent achievement gaps between wealthy and poor schools.