<![CDATA[The psychosocial adaptation of santri in Islamic boarding schools is increasingly challenged, especially for those from dysfunctional families. This condition affects behavioral stability, emotional regulation, and resistance to rules, impacting the effectiveness of character education. This study aims to analyze the psychosocial adaptation problems of santri and formulate adaptive, contextual, and humanistic educational intervention strategies. A descriptive qualitative approach was applied, using observation, in-depth interviews, and documentation. The subjects included santri from dysfunctional families and asatidz involved in their guidance. Results indicate that prior parenting experiences shape insecure attachment patterns (Attachment Theory) and low self-regulation skills (Self-Regulation Theory), influencing adaptation. Effective interventions include personal-emotional approaches, gradual and consistent guidance, reflective practices, and supportive social environments. Islamic boarding schools serve as spaces for psychosocial reconstruction and character development based on Islamic values. This study highlights the necessity of a humanistic, adaptive, and contextual approach to achieve transformative and sustainable character education]]>
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