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Drawing on developmental and policy research, this study examined whether 3 dimensions of caseworker–recipient interaction in welfare offices functioned as critical ecological contexts for recipient families. The sample consisted of 1,098 families from 10 welfare offices in National Evaluation of Welfare to Work Strategies (NEWWS). In multilevel analyses, caseworker support, caseload size, and emphasis on employment predicted 5-year quarterly trajectories of earnings, income, and welfare receipt. Recipients in offices characterized by high support had steeper increases in earnings and income; those in offices with high caseload size had steeper decreases in income and welfare receipt; and those in offices with high emphasis on employment had steeper decreases in welfare receipt. These economic trajectories were associated with children’s reading and math achievement and internalizing behavior at ages 8–10.