This study examined predictions from preschool parenting measures to middle childhood cognitive and socioemotional child outcomes to explore whether parenting assessment methodologies that require more time, training, and expense yield better predictions of child outcomes than less intensive methodologies. Mother-child dyads (N=278) in low-income African American families were assessed when the child was in preschool, using maternal report, the Home Observation for Measurement of the Environment-Short Form (P. Baker & F. Mott, 1989; R. Bradley & B. Caldwell, 1984), and structured observational measures of parenting. Child outcomes reported by children, mothers, teachers, and direct assessment were collected 4 years later. All parenting methodologies showed some predictive value; however, observational parenting measures showed the strongest and most consistent predictions of child outcomes.