The children of (im)migrants are the fastest growing population in U.S. schools at the same time there is increased anti-(im)migrant discourse, creating a unique linguistic ecology for its students. These multinational, multilingual, and multicultural students often encounter mononational, monolingual, and monocultural ideologies in their schools and communities. The result is that potentially hybridized learning contexts turn into sites of struggle for continued positive multilingual identities and investments. This multiple case study implemented surveys and interviews to explore the factors that contribute to the high multilingual investment of three self-identifying Mexican students residing in the U.S. Findings indicate that strong family relationships, formal coursework in Spanish, as well as a strong ethnic identity as Mexicans are interrelated factors that contribute to their high multilingual investment. In turn, this study suggests there are multiple pathways for Spanish-speakers residing in the U.S. to maintain, develop, and regularly use their Spanish abilities even in English hegemonic contexts. Dual language education is a powerful factor, but formal Spanish courses at the secondary and post-secondary level are also equally strong contributors when dual language education is not available. Furthermore, years of schooling in Mexico can counter monolingual educational contexts that adolescents often encounter. Implications for how educators may further facilitate positive and powerful multilingual identities and investments with their students along the educational pipeline are explored with a specific attention to Spanish language programming and raciolinguistic ideologies.