Despite mounting evidence that zero-tolerance policies do not deter misbehavior, teachers and administrators continue to respond to a range of student infractions through punitive measures, such as ticketing, expelling, and suspending students. Black boys, black girls, and Latinx students are most adversely affected by discipline in the era of mass incarceration. This article explores the staying power of punitive discipline by tracing how the Gun-Free Schools Act of 1994 (GFSA 1994) resulted in the emergence of harsh discipline systems and law enforcement in schools. It focuses on the ways GFSA 1994 ushered in a punitive infrastructure, law-enforcement entanglements, and school-based discipline policies and practices that inflict racial violence on black and brown children and youth. The following questions guided the inquiry: (1) How has GFSA 1994 shaped the discipline infrastructure of public schools in the United States? (2) How has GFSA 1994 created law-enforcement entanglements across the K-12 landscape? (3) How has GFSA 1994 influenced the function of discipline policies and practices on students by race and place 25 years after its adoption? and (4) What are the varied net-widening and net-deepening effects of GFSA 1994 across geography: urban, suburban, and rural? (Who is in more trouble, more often and finding it more difficult to get out of trouble?). Through presenting the net of social control that GFSA 1994 ushered in and its material consequences, this article conveys how school discipline reform will require a far-reaching policy agenda that is as bold and audacious as the tough-on-crime era policies that ushered in the era of mass incarceration.