The authors blended elements from the Stress Process Model and the Family Stress Model to investigate the direct and indirect effects of custodial grandmothers’ (CGMs’) coping resources (i.e., active strategies, passive strategies, and social support) on their psychological distress, their parenting practices, and their grandchild’s internalizing and externalizing symptoms. Participants included African American and White CGMs (N = 733, Mage = 56) who provided full-time care to a grandchild (Mage = 9.8). Structural equation modeling revealed that social support and active coping were related to lower CGM distress and less ineffective parenting, whereas passive coping was associated with increased distress and more ineffective parenting. Ineffective parenting had direct effects on grandchildren’s outcomes, whereas CGM coping resources had direct effects on ineffective parenting and indirect effects (through ineffective parenting) on grandchildren’s externalizing and internalizing difficulties. The authors conclude that CGM coping resources affect the psychological well-being of both generations.