In this article, we draw from the Civic Lessons and Immigrant Youth study to present key issues and implications related to teachers' work with immigrant youth. This synthesis draws on data and analyses from over six years of work examining the experiences, skills, and roles of teachers of immigrant youth as they navigated the complex terrain of teaching topics of citizenship in settings when not all youth had formal citizenship rights. Major themes include: the significance of building trusting relationships with immigrant students; the importance of approaches to teachers' knowledge building and legitimization of their immigrant students; and, finally, the prevalence of teachers' concern with the safety of their undocumented students. Subsequently, we pose questions for the field of teacher education in an era when immigration, education, and citizenship are intersecting in complex ways. Amid over-generalized conceptions of teaching for diversity, this article contributes to understanding how experienced teachers who supported immigrant rights practiced their craft, creating affirming environments in schools.