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What happens to multigenerational care when mobility is legally foreclosed? For undocumented immigrants who settle and age in the United States, midlife often coincides with peak responsibility for others: they are raising children in destination communities while their own parents grow old in communities of origin. Yet free and safe cross-border movement—central to sustaining family life—is precisely what legal precarity restricts. This study examines how undocumented status reshapes the social worlds of immigrants as they age into an undocumented “sandwich generation.” Drawing on three waves of longitudinal interviews with long-settled undocumented Mexican immigrants in Chicago (n=51), I analyze how participants navigated caregiving “here” and “there” as they transitioned from young adulthood into middle age. I find that undocumented status reshaped parenting in ways that shifted as children aged. When children were young, parents faced the greatest strain—juggling unstable work, limited access to services, and fears of separation while securing childcare, schooling, and health care. As children grew older and more independent, some pressures eased, and adolescents and young adults increasingly contributed economically and bureaucratically to household stability. At the same time, border enforcement and reentry bars prevented return travel, turning care for aging parents in Mexico into long-distance support maintained through remittances and coordination with relatives, with illness and death abroad revealing the emotional costs of absence. Midlife therefore concentrated opposing temporal demands: obligations to children gradually declined just as parents abroad required more care, while migrants’ own later-life plans remained uncertain in the absence of secure legal status or retirement protections. Together, these dynamics show how legal precarity reorganizes family support across generations, producing a form of aging in which immigrants stabilize others’ life courses while their own remains structurally suspended.