Many studies have highlighted the capacity of community arts programs to re-engage those young people considered at-risk of disconnection from future education and/or employment. "Evolution" is an artist-guided visual arts program established for young people challenged by mental health and social issues that aims to foster re-engagement in education and training. It was founded by a community-based youth arts studio, Signal, and in a partnership with a youth support service, has developed into an effective, strength-based model of practice that focuses on the young people's existing capacities and positive qualities rather than setting out to improve perceived deficits. Central to the success of this program has been the commitment to relationship-building, mediated through art practice, and the opportunities afforded to connect positively with others. This paper reports on research during the formative years of this initiative and outlines the conditions that framed and impacted upon participant engagement in the Evolution Program.