This research sought to identify a potential process by which intergenerational crime occurs, focusing on the effect of parental incarceration on adolescents’ subsequent arrests. We drew from Matsueda’s work on reflected appraisals as an explanatory mechanism for this effect. Thus, the present research examined whether caregivers’ and adolescents’ expectations for adolescents’ future incarceration sequentially mediated the effect of parental incarceration on adolescents’ actual arrest outcomes. Propensity score matching was used to examine this effect in a sample of 1,735 15- to 16-year-olds using NLSY97 data. Parental incarceration was positively related to caregivers’ expectations of adolescents’ future arrest. Moreover, caregivers’ expectations were strongly associated with adolescents’ expectations. Finally, the effect of parental incarceration on adolescents’ actual future arrest likelihood was partially mediated by caregivers’ and adolescents’ expectations for this outcome. This study revealed support for the proposition that the experience of parental incarceration may influence adolescents’ negative outcomes through reflected appraisals.