At Wentworth, rule violations are normally minor in nature and handled at the private school administration's discretion. A recent event involving the possession and use of alcohol during an off-campus school overnight activity leads to the development of a zero tolerance substance abuse policy. The zero tolerance policy is tested by one of the school's top students and her influential parents. This case study examines the possible impact zero tolerance policies can have on behavior management in a niche, private, secondary education institution. Related educational leadership issues include: zero-tolerance education policies; school organizational culture; punitive and restorative mechanisms of social justice; moral and ethical school leader decision-making; and the politics of education.