Objectives: It is imperative that individual differences in the cultural contexts of adolescent mothers, whose parenting is often linked to poor child outcomes, be better understood, especially among Puerto Rican-origin mothers who experience high rates of poverty. Behaviors that mothers use to elicit compliance from their children are important to investigate, because children’s ability to engage in regulated, compliant behavior has long-term consequences for their adjustment. This study tested whether mothers’ orientation to both American and Latino cultures influenced the associations between such maternal behaviors and compliant and defiant child behaviors. Method: The sample included 123 young, Puerto Rican-origin mothers and their 24-month-old toddlers. Behaviors coded from a toy cleanup task measured maternal guidance and control and child compliance and defiance, and acculturation and enculturation were measured with a self-report questionnaire. Results: Maternal guidance predicted more child compliance, with no significant variations by cultural orientation; however, mothers who were more enculturated had children who were more compliant. As predicted, mothers’ more frequent use of control was related to more child defiance for mothers reporting high levels of acculturation, and not for less acculturated mothers. Conclusions: Findings support the hypothesis that individual differences in cultural orientation influence variations in associations between certain maternal and child behaviors.