The intergenerational transmission of criminal behaviour is well-recognized, but less is known about the mechanisms that may explain it. This study presents new analyses from the Cambridge Study in Delinquent Development, which examine the intergenerational transmission of criminal convictions. It then investigates mediation via psychosocial risk factors. The convictions of fathers and mothers were significantly related to the convictions of their male offspring, and this was mediated via the fathers’ drug use. However, the convictions of fathers were only indirectly related to the convictions of female offspring via the father’s cohabitation problems. The convictions of mothers were also indirectly related to those of the female offspring through harsh parental discipline. Accurate identification of the role that psychosocial risk factors play in intergenerational pathways for males and females can inform much more effective gender-specific prevention.