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Detrimental circumstances (e.g., poverty) in the United States may affect parents, parenting, and children. As a result, children may be labeled “at risk” for school failure. To reduce risk, more school and school earlier (e.g., Head Start) is offered. This study examined whether teacher stress affected this schooling paradigm with regard to outcomes in child emotion regulation (ER). Chicago School Readiness Project (CSRP) data were reanalyzed, examining associations between stress, warmth, and ER. Head Start teachers were interviewed. The study asked (a) Do teachers exhibiting more warmth help children develop better ER? and (b) What are teachers’ lived experiences regarding child ER? Data demonstrated stress and warmth were associated with increased report of child dysregulation. Implications and insights are discussed.