Detrimental circumstances (e.g., poverty, homelessness) may affect parents, parenting, and children. These circumstances may lead to children being labeled "at risk" for school failure. To ameliorate this risk, more school and school earlier (e.g., Head Start) is offered. To improve child outcomes, Head Start teachers are expected to bolster children's academic readiness in a manner that is beneficially warm, circulating warmth in their classrooms to sustain positive teacher-child relationships and the positive climate of the classroom. The Classroom Assessment Scoring System (CLASS; Pianta et al., 2008) is one tool by which these domains of warmth are assessed. There are, however, significant personal and professional stressors with which Head Start teachers contend which the CLASS (Pianta et al., 2008) does not consider in its scoring methods. Uplifting the voices of six Head Start teachers, the present study implemented individual and focus group interviews during the summer and fall months of 2020 during the COVID-19 pandemic, asking (a) What were the stories, histories, and lived experiences of these Head Start teachers with regard to stress and warmth in a time of crisis? and (b) How did these teachers understand and approach the CLASS (Pianta et al., 2008) and its measures of their warmth? Data demonstrated Head Start teachers engaged in a type of performativity to 1) mask their stress, potentially worsening their levels of stress in order to maintain warmth for their students' sake, and 2) outwit the prescribed CLASS (Pianta et al., 2008) observations. Implications and insights are discussed.