AbstractThis study aimed to ascertain the impact of parent’s criminal justice involvement on offspring’s contact with the criminal justice system in Singapore. It further analyzed how various aspects of parent’s criminal justice involvement influence the extent of the intergenerational transmission. Linked administrative data of five full birth cohorts (1965, 1970, 1975, 1980, 1985; N = 93,829) and their children were analyzed (Nchildren = 183,015). Restricted mean survival time (RMST) analyses were conducted, and results suggested that children whose parent had contact with the criminal justice system had fewer crime-free years compared to children whose parent did not have any criminal justice contact. In addition, the impact of paternal and maternal involvement with the criminal justice system was greater on daughters than sons; the impact of custodial sentences was greater than that of noncustodial sentences; and it was also found that a higher frequency of parent’s criminal justice involvement increased the likelihood of children’s contact with the criminal justice system. Intergenerational transmission of criminal justice involvement was observed in Singapore, and so the findings highlighted the importance of supporting families of offenders to disrupt the negative cycle of offending behavior.