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Incarcerated juvenile offenders mandated into treatment in correctional settings are often characterized as “treatment resistant.” Despite the extensive literature and increasingly widespread adoption of evidence-based practices that address the treatment needs of this population (e.g., MST, DBT, T-CBT), there is little writing on the actual process of engaging juvenile justice-involved youth in productive therapeutic work. Yet, the stakes of low engagement and failed treatments are high – including chronification of delinquent behavior and risk of becoming further embroiled in the criminal justice system. Drawing on the writer’s training in Mentalization-Based Treatment for Adolescents (MBT-A) and Developmental-Relational Therapy (DRT), this paper will discuss population and setting-specific barriers to engagement and use composite case material to outline the “nuts and bolts” of setting up productive treatments with juvenile offenders with histories of developmental trauma including setting the frame, formulating goals, practical tools of engagement, and navigating inevitable ruptures in the therapeutic relationship.