The families of homeless young people are most often portrayed as a precipitating factor in their homelessness. However, recent studies, particularly those taking a longitudinal approach, have drawn attention to the enabling role of family members and their positive influence on the housing trajectories of homeless youth. Drawing on selected findings from an ongoing longitudinal qualitative study of homeless young people in Dublin, Ireland, this paper aims to build on this relatively fertile area of research. We demonstrate the supportive role of the families of young people who experience homelessness (often as a consequence of difficult family environments) and specifically examine how family re-engagement is negotiated and achieved. The findings highlight a number of dimensions of transition and change. Prominent among these is the importance of renewed trust and communication. Young people and their parents also had to accept responsibility for areas of life that previously served to undermine their relationships and were implicated in the circumstances surrounding a young person's premature home-leaving. Tensions and resistances on the part of young people are highlighted, demonstrating the adaptive mechanisms at work as they attempt to re-engage with family members. The implications of the findings for social work intervention with homeless youth are discussed.