Labeling theory suggests that criminal justice interventions amplify offending behavior. Theories of intergenerational transmission suggest why children of convicted parents have a higher risk of offending. This paper combines these two perspectives and investigates whether labeling effects might be stronger for children of convicted parents. We first investigated labeling effects within the individual: we examined the impact of a conviction between ages 19-26 on self-reported offending behavior between 27-32 while controlling for self-reported behavior between 15-18. Our results show that a conviction predicted someone's later self-reported offending behavior, even when previous offending behavior was taken into account. Second, we investigated whether having a convicted parent influenced this association. When we added this interaction to the analysis, a labeling effect was only visible among people with convicted parents. This supports the idea of cumulative disadvantage: Labeling seems stronger for people who are already in a disadvantaged situation having a convicted parent.