Engaging the silent adolescent is a major psychotherapeutic challenge. This article presents a comprehensive approach to this problem, illustrated with clinical material. This approach emphasizes a careful diagnostic assessment, including an assessment of the patient's level of personality organization and capacities to participate in psychodynamic psychotherapy. Three approaches to the silent teenager are explored in depth: a mostly supportive approach focused on containment of maladaptive behaviors; a psychodynamic approach with supportive elements focused on demonstrating safety through humor, play, normalization, and self-disclosure while exploring the patient's automatic relationship patterns; and a psychodynamic approach using transference-focused psychotherapy for adolescents (TFP-A), aimed at effecting long-lasting changes in the patient's views of self and others and their characteristic ways of managing conflict and stress, with gradual movement from a tendency for controlling, protective silence to vulnerable, cooperative sharing.