Joaquin, a 15-year-old Latino high school student, was arrested and removed from the Upward Bound (UB) program following a student-on-student sexual assault allegation. UB adopted a student-centered discipline approach that promoted socioemotional learning opportunities. However, the staff was regulated by complex state and federal policies and had not experienced severe student misconduct claims prior to 2018. This case illustrates how educational leaders grappled with disciplinary issues in a compensatory program with a strong pro-socioemotional learning policy. The case examines the legal, regulatory compliance, and policy issues that arise for leaders in upholding their commitment to socioemotional learning, while holding students accountable.