This conceptual article addresses the need for educators to interrupt status-quo silences surrounding the role of immigration status in schools--an issue that disproportionately impacts Latina/os. In this article we: (a) articulate the need for teacher education to address the impact of undocumented status in school settings; (b) present ethnographic vignettes of teachers who navigated these issues drawing from two qualitative studies; (c) synthesize understandings related to teaching undocumented youth; (d) highlight emerging areas of focus based on our research; and (e) outline continuing tensions in how teachers address documentation status. This article serves as an entry-way to bridge the lived circumstances of undocumented youth in schools, teacher practice, and aspirations for more equitable schooling.