The authors examined (a) differences in school engagement and the subjective well-being (SWB) of 330 Israeli students (Grades 7-10, 52% girls) in specialized school classes (arts and science) versus students in classes with no specialized subject and (b) the role of engagement as a mediator between class choice and SWB. A multivariate analysis of covariance examined intergroup differences and structural equation modeling was used to test the mediation model. The results indicated that students in both specialized classes felt more engaged than students in regular classes and that students in science classes experienced higher SWB than did students in art and regular classes. The difference between specialized classes and regular classes in terms of student SWB was fully mediated by student engagement. The results suggest that educators and policymakers should consider enabling students to enroll in specialized classes that may not only increase their engagement but also their SWB.