Drawing from a multi-year ethnography of a Latino/a immigrant Pentecostal church and from high school observations and interviews of three focal students, this article compares the language and literacy experiences of an immigrant Mexican Pentecostal adolescent in church and school contexts. I document how the youth's Sunday school class fostered a collective, supportive, and caring environment while his high school was marked by isolation, alienation, and hostility. The church afforded him opportunities to engage in rich language and literacy practices, and through his participation he became a competent member of the church. In contrast, his language and literacy classes at school were characterized by a lack of effective instruction and a watered-down curriculum. Sociocultural theory and critical pedagogy serve as frameworks to shed light on how schooling is embedded in the social, cultural, and political context. Implications and recommendations for schools, teachers, and administrators are offered.