Guided by an ecological perspective on family policy, this qualitative study used family life history interviews to document the legal and policy dilemmas faced by 26 grandparent caregivers residing in Montana. Most grandparents (n = 18) were caring for their grandchildren in informal or private care arrangements. Findings revealed four legal or policy contexts that hindered informal grandparent caregiving, including the lack of a kinship care navigation system, the lack of legal rights, fear of the child welfare system, and disparities between informal and formal kinship care policies. Future policy directions, including expanding subsidized guardianship programs and granting informal grandparent caregivers' legal authority over their grandchildren, are discussed.