This article examines whether prisoners’ children have more adult convictions than children whose parents were convicted but not imprisoned. This is investigated in England and the Netherlands from 1946 to 1981 using two prospective longitudinal datasets: the Cambridge Study in Delinquent Development and the NSCR Transfive Study. In the Netherlands, no significant relationship was found between parental imprisonment and offspring offending. In England, a relationship was found for sons only. This association can be partly explained by parental criminality. However, after controlling for number of parental convictions and other childhood risk factors, a significant relationship remained between number of parental imprisonments and sons’ offending. When parental imprisonment at different ages is examined, parental imprisonment only significantly predicted sons’ offending when it happened after the sons’ seventh birthday.