A number of recent studies have examined cross-generational continuity in parenting behaviors using long-term prospective data sets with multiagent, multimethod designs and have found significant but relatively modest associations. Key questions remain regarding additional influences on parenting practices that may help to account for discontinuity in parenting across generations. The present study focuses on fathers’ parenting, specifically ineffective and harsh discipline practices, for an at-risk sample of men (the Oregon Youth Study sample) and is based on a dynamic developmental systems model approach to problematic family functioning. The model points to the importance of developmental systems, including the risk context in which the family lives and key influential social interactional systems. Influence that is directly pertinent to the outcome of interest is emphasized; thus, we studied the extent to which the young mother’s developmental risk and poor and harsh discipline practices might influence those of the young father. Findings that risk context and maternal discipline practices increase the risk that the young father will use poor and harsh discipline practices indicate the importance of the focus on influence dynamics across parents.