This article describes a model designed to engage very high-risk pregnant and parenting young mothers who are not traditionally served by home visiting or other young parent programs. These disengaged young mothers do not live in stable environments: they are street or gang involved, in danger of dropping out of school or have already dropped out, court involved, struggling with substance abuse and mental health issues, involved in domestic violence situations, and/or are isolated immigrants and refugees. They are at very high risk for long-term negative adult outcomes, including unemployment, systems involvement, and long-term poverty, increasing the likelihood of negatively affecting their children. This model utilizes engagement strategies to intentionally find these young mothers and retain them in programming over long periods of time. These engagement strategies, developed based on Prochaska's stages of change model, include relentless outreach, transformational relationships, and stage-based programming. Through the implementation of these strategies, 81 very high-risk young mothers were identified and served in the Circle of Care Project. The participant retention rate was 90%. Implications suggest that very high-risk young parents can be good candidates for programming to improve their lives and the lives of their children, as long as that programming is developmentally appropriate and incorporates a strong relationship-building component.