Abstract Objective We examined the directionality among child routines, noncompliance, parental stress, and harshness using a cross‐lagged model. Background Child routines foster development and are associated with lower noncompliance and parenting stress, correlating with less harsh discipline. Transactional parent–child interactions imply bidirectional associations warranting thorough analysis. Method The study used data from Years 3 and 5 of the Future of Families and Child Wellbeing Study ( N = 2,353; 48% female). Child routines, noncompliance, parenting stress, and harsh parenting were reported by mothers. Results Child routines at 3 years old predicted a decrease in noncompliance at 5 years old (β = −.04, p < .001), but not the reverse (β = −.01, p = .54). Noncompliance at 3 years old predicted parenting stress at 5 years old (β = .05, p = .007), and parenting stress at 3 years old predicted harsh parenting at 5 years old (β = .07, p < .001). Parenting stress (β = −.06, p < .001) and harsh parenting (β = −.05, p < .05) at 3 years old predicted fewer routines at 5 years old, but routines did not predict stress or harsh parenting. Conclusion Promoting child routines at a young age may be associated with improved compliance behaviors in children. Reduced compliance issues may lower parenting stress, which can decrease the use of harsh parenting practices. Implications The findings suggest that interventions promoting child routines could foster positive behavior and reduce parenting stress, ultimately contributing to healthier parent–child relationships and better developmental outcomes for preschoolers.