We examined relations between positive parenting, parenting stress, and children's regulatory abilities across infancy and early childhood. First-time mothers and their infants (N = 682) were recruited prenatally. Mothers belonged to one of three potential demographic risk groups: adolescent mothers (AM), adult low-educated mothers (LEM), and adult high-educated mothers (HEM). Parent-child interactions were observed in the home and scored for positive parenting (at 4, 8, and 18 months) and child self-regulation (at 4, 8, 18, and 30 months). Parenting stress was measured by questionnaire at 6, 12, and 24 months. A multigroup cross-lagged panel model indicated different patterns of effects for adolescent and adult mothers: for AM, positive parenting and parenting stress were related early in infancy, but no relations emerged with regulation until 18 months. For LEM, parenting related to regulation only at later ages, and for HEM, positive parenting, parenting stress, and regulation were associated early in the infant's life but not later. Differing patterns of influence indicate, perhaps, the importance of considering demographic risk and timing of parenting in childhood in relation to child regulatory outcomes. (PsycInfo Database Record (c) 2022 APA, all rights reserved).