This article considers how immigrant retention relates to family obligations, drawing a complex portrait of a common family dilemma involving the care of aging kin. The ethnographic life-history approach offers an important perspective on how health and well-being are not simply structured by formal access to institutions of care, but by the socio-cultural, economic and geographic flexibility of families to accommodate their needs. Analysis draws on the interdependant migration histories of a family of six adult sisters originating in Tanzania. In the case of this family, the dilemma surrounding the care of aging parents is not so much caused by migration's disruption of traditional filial obligations. Instead, it is the effect of social pressures stirred in both sending and receiving countries, which frame opportunities for eventual social integration, relocation or sometimes reluctant repatriation. A reflexive approach argues for the active presence of ethnographers in policy debates.