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Utilizing Stanton-Salazar’s (2011) empowerment social capital theoretical framework, this qualitative study explores the various roles, practices, and challenges of 14 classroom teachers working to increase the college-going rates of working-class Latina/o youth, as well as extending their work to simultaneously challenge educational and social inequity (i.e., empowerment agents). Many of the findings from the interviews, documents, and journals suggest several factors for stepping into these roles, one of which includes the teachers’ own racial, ethnic, and class identities as driving forces. Despite the multiple practices shared by participants, many teachers in the study faced ongoing burnout and a lack of sustainability. Several policy and practice recommendations are also offered in the paper.