Purpose: Racial inequality in school discipline is an important challenge facing educational stakeholders. There is little research on how educators exercise discretion in navigating the disciplinary process from perceived misbehavior to disciplinary consequences. Research Methods/Approach: This study draws primarily on semistructured interviews with district leaders, school administrators, and teachers in an urban emergent district in the southeastern United States to examine how principals, assistant principals, and teachers relate to and interact with each other in determining students’ disciplinary consequences. Findings: The findings illustrate the variation of administrators’ disciplinary philosophies across interventionist, interactionalist, and noninterventionist tendencies. Relationships and interactions among school leaders and teachers are a major component of the organizational dynamics underlying how perceived misbehavior is handled in schools. School-level decisions about the generation and adjudication of office discipline referrals are the product of interactional patterns and relationships among adults in schools that partly shape discretion and accountability in disciplinary decisions. The findings unearth two key tensions—disciplinary philosophical tensions and discretion and accountability for office discipline referrals tensions—among district leaders, school administrators, and teachers navigating referrals and further disciplinary consequences. Implications: More intensive on-the-job support for both school leaders and teachers is needed to reduce racial inequality in suspensions. Developing the professional capacity of teachers and school leaders through mentoring, coaching, and professional development is crucial to replacing exclusionary discipline with nonpunitive practices. Districts ought to prioritize supporting school leaders in developing and expanding their professional capacity, who in turn support teachers in addressing school discipline challenges.