This multiple-case study probes the social-emotional well-being of elementary and middle-grade students labeled as English learners who were enrolled in different bilingual program models in the midwestern United States. Using ecological systems theory, this qualitative study probes students’ social-emotional well-being across schools and within different bilingual program models, seeking to determine the structures and practices that nurture positive facets or perpetuate negative facets of student well-being. Findings indicate that interactions with peers and adults in schools influence students’ social-emotional well-being, with program-model variations, community demographics, and societal discourse shaping these in-school experiences, relationships, and sentiments. Implications center on critical consideration of bilingual program-model implementation to prepare teachers, promote schoolwide integration, prioritize home languages, and nurture inclusive communities.