Grandparent-headed families, called grandfamilies, are increasingly important in assisting adult children and grandchildren. This study (N = 376) provides a qualitative analysis of statements made by grandmothers about relationships between three core family members: (a) grandmother, (b) parent, and (c) grandchild. These family members constitute an intergenerational triad, displaying a variety of relationship patterns based on emotional closeness or distance. The most common configuration in three-generation families was all-three inter-generational members emotionally close or connected, and comments about relationships reflected problem solving, communication, and emotional management. Families in which the parent was close to and linked both adjacent generations were also frequent, and comments showed a clear parenting hierarchy with grandmother as secondary. Few families had weak, disconnected relationships between all three triad members or an emotionally isolated parent: These patterns were related to low grandmother and grandchild well-being. Evaluating intergenerational relationships aids identification of at-risk grandfamilies and has implications for family interventions. (Contains 5 tables.)