Purpose: Transitions in caregiving, such as becoming a primary caregiver to grandchildren or having adult children and grandchildren move in or out, may affect the well-being of the grandmother. Design and Methods: This report describes caregiving patterns at 3 time points over 24 months in a sample of 485 Ohio grandmothers and examines the effects of stability and change in grandmother caregiving roles (raising a grandchild, living in a multigenerational home, or not caregiving to grandchildren). Drawing on the Resiliency Model of Family Stress, the study examined caregiving stress and reward, intrafamily strain, social support, resourcefulness, depressive symptoms, mental and physical health, and perceived family functioning. Caregiver group, time of measurement, switching between caregiver groups, and baseline age, race, education, work status, and marital status were considered as independent variables within the context of a one-way treatment structure in a mixed-model multivariate analysis. Results: There were significant caregiver group effects for all variables, except mental health and resourcefulness. Grandmothers raising grandchildren reported the most stress, intrafamily strain, and perceived problems in family functioning, the worst physical health and more depressive symptoms, and the least reward and subjective support. Across groups, there were significant time effects, with worsening physical health and increased stress over time. Switching to higher levels of caregiving was associated with worsening physical health and increases in stress, intrafamily strain, and perceived problems in family functioning. Implications: Recommendations for research and for practice, especially during times of caregiving transition or for grandmothers raising grandchildren, are discussed.