Parenting stress in grandmother caretakers has not been directly compared with a matched sample of mothers in the caretaker role. This study examined the main and interaction effects of caretaker status, employment, and race on parenting stress and whether these factors affect parenting stress in a convenience sample of grandmothers raising grandchildren (n = 86) and a sample of mothers of preschoolers (n = 86), matched for women’s partner status, race, and employment. Grandmothers raising grandchildren reported more overall parenting stress and parental distress than mothers. Non-employed women reported more negative perceptions of their children and more difficult interactions with them. When controlling for contextual variables, grandmother caretakers showed greater parenting distress, but employment was not related to parenting stress. Being Caucasian and caretaking of older children affected overall parenting stress, parent-child interactions, and perceptions of one’s children. Future research needs to consider the effect of outside influences on grandmothers’ stress.