This grounded theory study of how Title I middle school administrators determine students' punishments was developed using interviews with 27 Florida administrators from schools allowing corporal punishment. Administrators' choices were shaped by their upbringings, their experiences as parents, their job requirements, the expectations of students' parents, and fears of reprisal. They expressed simultaneous desires to develop the child while deterring future misbehavior. They described the outcomes of their decision making as emotional work that entailed contradictions and compromises. To encourage positive preventive and responsive school discipline practices, policies must address administrators' misconceptions about ineffective practices by providing both pressure and support for change.