Puerto Rican students are a growing population in U.S. mainland schools, yet few recent studies have focused on the school contextual and identity-based experiences of Puerto Rican youth. Using stage-environment fit and LatCrit theories, this qualitative study examined seven Puerto Rican adolescent students' perspectives on domains of school context, along with prominent aspects of how they defined "being Puerto Rican," in two urban middle schools. Based on qualitative analyses of student interview and focus groups, findings revealed that students' experiences with teachers, ethnic-racial climate, and sense of belonging were fundamentally contradictory, where examples of purported "equal treatment" were tempered by racialized experiences marked by stereotypes and the suppression of Spanish, especially among male students. However, dimensions of identity-based resiliency such as ethnic pride, sense of "familismo" with other Puerto Rican students, and being bilingual emerged as sources of strength. We discuss school-based possibilities for the delivery of critically conscious support and ethnic affirmation for students during this critical developmental period, based on our exploratory findings.