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In mental health settings, we often meet traumatized and volatile youth who resist treatment and do not respond to engagement attempts. For such patients, the treatment refusal may be a representation of their level of personality organization; it can represent difficulties to relate to others, to regulate affective experiences, and to integrate different self-states. Using a case study of a treatment resistant adolescent in residential care, I discuss the limitations of engagement techniques with patients at the lower end of personality organization and argue that engaging “difficult to treat” adolescents requires a clinical shift from the therapeutic encounter to the development of a system-based “holding” environment. I present a modified intervention model that integrates psychodynamic formulation of personality development with process-oriented systemic work. The model described emphasizes the role of the therapist as the initiator and facilitator, helping to construct a coherent and attuned environment within the residential care system. Through case vignettes, I provide examples for the clinical shift from the therapeutic encounter to the environment of the ward and demonstrate how developing a holding environment can overcome engagement barriers and support the development of the patient’s ego capacities, sense of self, and object relations.