Many troubled youth show developmental problems in attachments to family, school, and community. Past experience causes them to be reluctant to trust adults as reliable mentors and life teachers. Attachments are repaired and strengthened by establishing healthy relationships. Secure belonging is the foundation to the development of autonomy and self-control. The twin challenges of attaching and being autonomous are vital to a successful life. This article describes the complexity of creating relational connections in skillful work with children and youth. Relationships occur at three levels: (1) connections of trust; (2) connections to the ecology; and (3) the deep alliance. Workers with limited experience will find the struggle to create trusting bonds a sufficient challenge for their developing expertise.