Though surveys repeatedly demonstrate that most women who are homeless alone have minor children living apart from them, there is little information on the circumstances of their separations or whether and how they remain involved with their children. Analysis of data from in-depth interviews with mothers, relatives caring for their children, and shelter and child welfare staff highlights a tension between perspectives and aspirations of mothers and the agendas and social processes through which institutional systems manage the family life of women marginalized by homelessness and disability. Though women’s agency is evident in their efforts to maintain parenting roles, without facilitating resources and supportive structures, agency is often reduced to unpalatable choices among constraining alternatives. We consider how service systems might mitigate barriers to mothering as well as broader changes needed to genuinely support women’s aspirations for themselves and their families.