Using data from the Rochester Youth Development Study, a series of regression models are estimated on offspring problem behavior with a focus on the interaction between parental history of delinquency and the parent–child relationship. Good parenting practices significantly interact with the particular shape of parental propensity of offending over time, functioning as protective factors to protect against problematic behaviors among those who are most at risk. The moderation effects vary slightly by the age of our subjects. Accordingly, it is important to distinguish the effect of not only the level of parental delinquency at one point in time but also the shape of the delinquency trajectory on outcomes for their children. Good parenting holds the hope of breaking the vicious cycle of intergenerational transmission of delinquency.