My dissertation examines how low-income, urban African American caretaking grandmothers' coping strategies are affected by what these grandparents perceive and define as stressful, their individual and child-rearing goals and objectives, the formal and informal institutionalized resources they have available, how they make use of resources, and laws and policies that influence their care giving experience. Although numerous scholars have investigated the effects care giving have on the mental, physical, and economic well-being of grandparents and their grandchildren, researchers have devoted minimal attention to strategies grandmothers employ to minimize the disparity between their families' needs and the resources available to address them. I use ethnographic and in-depth semi-structured interviews to explore and describe the coping strategies of fifty grandmothers who are the primary custodians of their grandchildren residing on Chicago's Southside. I demonstrate that coping trajectories vary and offer insights into factors that account for this variation. I discovered that in order to ensure their family's survival, caretaking grandmothers must: (1) make institutional decisions concerning the type of care-arrangement needed to enable them to function as primary and sole caretaker of their grandchildren; (2) manage the role of state intervention in their uphill battles to bring stability to their families; (3) devise parenting practices that address children's higher order needs, including addressing any prior history of abuse and/or trauma they may have experienced; and (4) compose a life in the wake of raising their grandchildren by shifting their expectations and behaviors concerning intimate, social, and familial relationships; labor market participation; lifestyle; and future plans. Furthermore, the research shows that coping trajectories are complex, unremittingly difficult, and offer a remarkable testament to the ways in which individuals manage to survive and in some cases thrive in the face of urban poverty and multiple forms of institutional oppression even as they age and wrestle with multiple caretaking issues. By making theoretical and empirical contributions to a range of sociological subfields, the research illustrates how coping strategies shape, and are shaped by, familial, community, and broader social, economic, and political processes. (author abstract)