Studies have often linked parenting to children’s subsequent antisocial behavior; however, the circumstances under which this might occur are less clear. The current study explores patterns in mothers’ parenting practices, and associated correlates including maternal delinquency and offending, mental health, and children’s physical aggression. This study is based on the first wave of the ongoing Vancouver Longitudinal Study; the objective of this prospective study is to identify the early risk and protective factors for aggression and violence from the earliest developmental periods. Parenting practices of 287 mothers with preschoolers are examined using a series of latent class analyses. Three different patterns of parenting emerged: Positive, Negative, and Intermittent. Patterns identified are associated with several key criminogenic, socio-demographic, historical, and developmental factors including current maternal adult offending, mothers’ mental health, ethnicity, and frequency of children’s physical aggression. Importantly, mothers who show parenting in line with the more negative classes also rely on a number of positive practices. Implications of the study suggest that parenting is influenced by mothers’ immediate situations and contexts (e.g., current offending rather that past delinquency), which can be targeted for intervention.