This study of Peninsula Youth Connections, a program operated in the Frankston Mornington Peninsula region by the Brotherhood of St Laurence and TaskForce, found that not only life circumstances but also systemic education barriers made it difficult for some young people to engage in meaningful learning. While the intensive case management and flexible approach of PYC were affirmed by youth professionals, the research also pointed to the need to clarify responsibilities and overcome boundaries between services involved in addressing young people’s multiple needs.