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This qualitative study examined factors within the school context that are salient to Puerto Rican students when accounting for their middle school experiences, as well as the significance of Puerto Rican ethnicity. Semi-structured interviews and focus groups were conducted with seven students in two urban schools. Analyses revealed that teachers, sense of belonging, and ethnic climate were important category dimensions of students’ experiences, but a pattern of contradictions within each was revealed. In particular, supportive teachers evidenced mediocre expectations, along with racialized behaviors. Positive aspects of Puerto Rican identity, such as language brokering and ingroup connection were noted, yet all students reflected an awareness of negative ethnic stereotypes. Findings have implications for offering culturally affirming support for students in schools.