Recent educational policy reports in the U.S. have called for significant changes in teachers’ work to increase their effectiveness. The paper examines the relationship between the restructuring strategies in two comprehensive high schools and teachers’ engagement, which is defined as a multi-dimensional construct. In one school, the restructuring strategies focused on creating a supportive climate for students, and in empowering students and teachers; in the other, emphasis was on developing professional skills of the faculty and strengthening group cohesiveness. The implications of the strategies for teacher engagement are illustrated with case study data. The discussion points to several conclusions: (1) the effects of restructuring are more bounded than is often assumed; (2) a quality of work life framework drawn from the social scientific literatures is useful for analyzing the effects of reform policies on teachers’ work; (3) teachers make trade-offs between different types of engagement in order to increase their work satisfaction; and (4) restructuring has potential for increasing teachers’ engagement in schools with mixed socio-economic and racial populations.