This article analyzes the narrative experiences of Hmong American adolescent males who were labeled at risk or high risk for academic failure or underperformance by their predominantly White school counselors and teachers. Additional data sources included classroom observations at two racially diverse public high schools and semi-structured interviews with two White American female classroom teachers to ascertain how the "at-risk" label manifested in everyday practices ranging from classroom management/discipline methods, instructional decisions, interpersonal interactions, referrals, and tracking practices. The findings will highlight how the "at-risk" label along with a range of other deficit-based expectations intersected with several problematic assumptions about Asian American masculinities and Hmong American culture that suggested that in general, White school personnel were not aware of how their understandings of racial deviance and difference shaped how they assessed, diagnosed, and interacted with these students. Critically, the "at-risk" label had direct implications for tracking the youth participants into non-college-preparatory tracks including pathways toward alternative, remedial, and special education, or in one case, juvenile detention. Implications are offered for practice and theory.