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Homophobic bullying is a pervasive issue in U.S. schools. Broadly, two distinct approaches to address bullying include punitive versus supportive practices. Few studies have considered these approaches in the context of school connectedness in relation to homophobic bullying. Drawing from theories of social support and control, we argue that supportive practices should reduce homophobic bullying and promote school connectedness. Further, although punitive practices may deter homophobic bullying, they also compromise school connectedness, except perhaps among students who have been bullied. Supportive practices could be especially important for promoting school connectedness for students who experience homophobic bullying. Using teacher (n = 62,448) and student (n = 337,945) data from 745 high schools that participated in the California School Climate Survey and the California Healthy Kids Survey, our study examines the association between teacher reports of punitive versus supportive practices, and student experiences of homophobic bullying and school connectedness. We also interrogate differential effects of punitive and supportive practices on school connectedness for students who have and have not experienced homophobic bullying. Results indicate that supportive, but not punitive, practices are associated with less homophobic bullying and higher school connectedness. Supportive practices also serve as a protective factor for students who have experienced homophobic bullying. Additionally, students in schools with less supportive practices, and who have not experienced homophobic bullying, report low levels of school connectedness comparable with students who have been bullied. Implications for school policy related to supporting students at risk for being bullied and school disconnectedness are discussed.