This dissertation consists of three papers that examine the complexities in upward intergenerational support and adult children’s influence on older adults’ health in changing family contexts of America and China. The prevalence of “gray divorce/repartnering ” in later life after age 55 is on the rise in the United States, yet little is known about its effect on intergenerational support. The first paper uses the life course perspective to examine whether gray divorce and repartnering affect support from biological and stepchildren differently than early divorce and repartnering, and how patterns differ by parents’ gender. Massive internal migration in China has led to increased geographic distance between adult children and aging parents, which may have consequences for old age support received by parents. This topic has yet to be thoroughly explored in China, as most studies of intergenerational support to older parents have focused on the role of coresident children or have not considered the interdependence of multiple parent-child dyads in the family. The second paper adopts the within-family differences approach to assess the influence of non-coresident children’s relative living proximity to parents compared to that of their siblings on their provision of support to parents in rural and urban Chinese families. The study also examines how patterns of the impact are moderated by parents’ living arrangement, non-coresident children’s gender, and parents’ provision of support to children. Taking a multigenerational network perspective, the third paper questions if and how adult children’s socioeconomic status (SES) influences older parents’ health in China. It further examines whether health benefits brought by adult children’s socioeconomic attainment are larger for older adults with lower SES and whether one of the mechanisms through which adult children’s SES affects older parents’ health is by changing their health behaviors. These questions are highly relevant in contemporary China, where adult children have experienced substantial gains in SES and play a central role in old age support for parents. In sum, these three papers take the life course, the within-family differences, and the multigenerational network perspective to address the complexities in intergenerational support and older adults’ health in diverse family contexts.