The word ‘discipline’ is used to mean either the punishment following disobedience or training in self-control, and schools use both methods when responding to student misbehavior. Currently, we do not know how elementary-age students and their families feel about both types of experiences, and which discipline practices they think ought to be changed or retained by their school. Using ecological and critical race theory frameworks, this phenomenological study aimed to listen to stakeholder voices to understand how students and caregivers experience school discipline practices in order to help determine culturally valid and ecologically sound disciplinary interventions in the future. Focus groups were conducted with 22 students and 14 caregivers at a public charter elementary school serving primarily African American students. The sample included participants whose experiences with school discipline practices ranged from those who have never received an office discipline referral to those who have received over 75 in one year, and a corresponding group of caregivers. Responses were analyzed inductively. Themes were grouped into three main dilemmas that the stakeholders are facing with regard to school discipline: the appropriate roles for school and family, the type of consequence to use, and how time should be allocated for different types of disciplinary responses. These findings highlight the complexity of school discipline beyond simple behavioral contingencies and reflect a need for continued collaboration between the school, students, and caregivers to co-create context-specific discipline policies and procedures.