Objectives: This paper set out to contribute to the literature by linking research into offending pathways with the study of longitudinal effects and intergenerational transmission of mental health. Methods: Data was used from two generations of the Cambridge Study in Delinquent Development, a longitudinal study of 411 men from London and their children who were followed since 1961–62. Results: Findings from this study (1) indicate that symptoms of depression and anxiety were highest among those who commenced offending in adulthood and (2) demonstrated familial continuity of mental health: poor offspring mental health was related to father's criminality, but not to their offender group. Conclusions: A thorough understanding of the heterogeneity of offenders is essential for policy and practice. It is suggested that future research further examines individuals who only commence offending in adulthood, since they have been shown to not only face a variety of adverse outcomes themselves, but are also likely to have children with distinct patterns of internalizing problems.