The expansion of student legal entitlements has been accompanied by the increasing formalization and institutionalization of school discipline. As educators’ discretionary authority over school discipline has been challenged and undermined, counterproductive authoritarian measures such as zero-tolerance policies have been implemented in its place. But to be educationally effective, school discipline requires that educators have moral authority and students perceive their actions as legitimate and fair. Ironically, the expansion of student legal rights, rather than enhancing youth outcomes, has increased the extent to which schools have relied on authoritarian measures, decreased the moral authority of educators, and diminished the capacity of schools to socialize young people effectively.