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Grounded in person–environment fit theory, this study examined whether low-income mothers’ preferences for education moderated the effects of employment- and education-focused welfare programs on children’s positive and problem behaviors. The sample included 1,365 families with children between ages 3 and 5 years at study entry. Results 5 years after random assignment, when children were ages 8–10 years, indicated that mothers’ education preferences did moderate program impacts on teacher-reported child behavior problems and positive behavior. Children whose mothers were assigned to the education program were rated by teachers to have less externalizing behavior and more positive behavior than children whose mothers were assigned to the employment program but only when mothers had strong preferences for education.