This article applies Bateson’s concept of the double bind to the interpretation of emergent problems in custodial grandmothers’ relationships with their other adult offspring and non-custodial grandchildren. The article suggests that women raising grandchildren are placed in a double bind situation in which the two core family values of caring for family members in need and treating all family members equally are in conflict. This conflict of interests is at the heart of many problems within the intergenerational family context and is experienced as both inescapable and distressing by both grandmothers and their adult children. Brief vignettes from two participants in a small-scale qualitative study of New Zealand custodial grandmothers’ lives are presented to illustrate this dynamic.