With rising attention toward the plight of children with incarcerated parents, there has, as yet, been little focus placed on the adults who care for them, individuals who may have a profound impact on the children's relationships with their incarcerated parent. This study explores unique parenting challenges the caregivers faced, from their perspectives and presents their voices. Caregivers discussed the strain of serving as a gatekeeper between the child and imprisoned parent, coping with stigma and isolation, and negotiating a predominantly child-unfriendly visitation system. The findings suggest that caregivers need information about raising a child in this context, connections with others in similar situations, and a more child-friendly and transparent judicial and visitation process.