The transition from adolescence to adulthood is a significant developmental stage. When foster youth age out of the child welfare system, they are at risk of having to transition without family support. This chapter applies the life course perspective to describe the theoretical and contextual foundation that explains the hardships foster youth experience when emancipated from the US child welfare system. Next, the theoretical basis for natural mentoring among foster youth is explored using the resiliency perspective to frame the discussion. Then, current research on natural mentoring among foster youth is reviewed. Implications are drawn for US child welfare practice, policy, and research with respect to how to improve outcomes for youth who age out of foster care through the cultivation of natural mentoring relationships. The chapter concludes with an examination of systems in place to support transitioning foster youth from England, Israel, and Australia.