Using the first-three waves of the Fragile Families and Child Well-Being Study, this paper examined factors affecting the first-three years of parenting among mothers, especially adolescent mothers, which included characteristics of the mother, child, and social context. Parenting was measured by engagement activities and the use of spanking as a disciplinary measure. The findings indicate that engagement activities between mothers and children were high over the first-three years and that their use of spanking was low at first but increased over time. Adolescent mothers were found to be more likely to spank their children when they misbehaved. The findings from regression analyses revealed that the first-three years of maternal parenting were associated with characteristics of the mother, child, and broad contextual environment, indicating the complexity and variability of factors associated with early parenting. Policy implications are discussed.