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This study examines how school social workers are both positioned and pressured to enforce zero-tolerance policies and attendance-focused interventions at the expense of advocacy-driven, student-centered support. Rooted in broken windows theory, these approaches undermine school effectiveness by fostering punitive climates and eroding student trust, engagement, and belonging. Using collaborative autoethnography, the authors reflect on their experiences navigating the tensions between institutional compliance and transformative, justice-oriented practice. Via critical reflection, this dialogic mechanism underscores how social workers can unintentionally reproduce exclusionary systems. The authors offer frameworks for reimagining school-based support roles that position social workers as champions of promoting, institutionalizing, and implementing restorative principles to disrupt disciplinary disparities, cultivate student belonging, and strengthen the overall equity and effectiveness of educational systems.