Homeward Bound shows that as family structure becomes more complex, so too does elder care, and existing institutions and legal approaches are not prepared to handle those complexities. As 79 million American Baby Boomers approach old age, their diverse family structures mean the burden of care will fall on a different cast of family members than in the past. Our current approaches are based on an outdated caregiving model that presumes life-long connection between the parents and offspring, with the existence of high internal norm cohesion among family members providing a valuable safety net for caregiving. Single parent and remarried parent-led families are far more complicated, fragile, and point to the need for increased formal support from the religious, medical, legal, and public policy communities. We base our analysis on in-depth, qualitative interviews with surviving grown children and stepchildren whose mother, father, stepparent, or ex-stepparent died. Their stories illustrate the profound ways that the caregiving, mourning, and inheritance process has changed in ways not adequately reflected in formal legal, medical, and religious tools. The solutions center on awareness and preparation: providing more support for individual planning for incapacity and death and, even more importantly, creating legal, political, and social planning for the graying of America at a time of increasingly complex familial ties.