There is broad consensus that strong educator-student relationships are important in improving outcomes for children coping with trauma and toxic levels of stress, and emerging evidence that positive relationships can help buffer against the compassion fatigue and burnout that is associated with working in high-needs schools. Through a case study and semi-structured interviews with 21 educators spanning a range of roles, in one K-12 charter school, in a large Midwestern city, we examine the relationship-building strategies utilized, perceived barriers to relationship building, and perceptions of emotional labor and stress. Results show that although all staff members prioritize relationship building, few were knowledgeable of strategies that were effective for building relationships with emotionally and behaviorally dysregulated students. The gap between their desire to build relationships and perceived low quality of relationships with students was both caused by and resulted in a high level of compassion fatigue and burnout. Implications for building educators' knowledge of relationship-building strategies are discussed.