Previous research has demonstrated that grandparent caregivers experience high levels of physical, psychological, and relationship stress. However, few studies have examined how psychosocial and relationships. perspective, this exploratory study examined predictors of parenting satisfaction and family functioning among 40 grandmothers raising grandchildren. Parenting satisfaction was associated with lower levels of financial burden and better family functioning. More optimal family functioning was associated with higher parenting satisfaction, more social support, and grandmothers’ mental health (i.e., less depression and anxiety). Unexpectedly, higher financial burden was also associated with better family functioning. Findings suggest that the quality of custodial grandmothers’ family relationships is influenced by both individual and contextual factors. However, because social support and financial burden had the strongest influence, practitioners should pay particular attention to the impact of contextual factors on the quality of relationships within grandparent-headed families.