A child's adjustment to the death of a parent is greatly influenced by the surviving parent's ability to attend to his or her own grief-related needs, to create and sustain a consistent and nurturing environment, and to encourage the child to express distressing or conflicting thoughts, feelings, and fantasies about the loss. Yet, the surviving parent's grief often compromises their ability to parent consistently and empathically. This article will illustrate how, by providing a holding environment for whole families, clinicians can help parents to facilitate children's grief reactions and, thus, mitigate long-term adverse mental health outcomes. Family Matters programs, designed and implemented in a community agency, use a holistic approach to family support and treatment in a milieu setting. Combining therapeutic work with surviving spouses and bereaved children supports children's grief while facilitating newly single parents as they adapt the structure of family life. When clinical work with families begins before the ill parent dies, the clinicians may build a relationship with the dying parent, prepare the child and surviving spouse for life after loss, and support continuity in family culture. We introduce a curriculum for simultaneously supporting bereaved children and parents, present a series of common challenges faced by surviving parents, and suggest avenues for intervention research.