The authors investigated whether prisoners who had a parent in prison, “second-generation prisoners,” had poorer rates of adjustment compared to those inmates who did not report a history of parental incarceration. Among a sample of 459 men and women in prison, approximately half reported having had a parent in prison or jail. There was considerable self-reported childhood adversity within the entire sample, with relatively higher levels reported by the second-generation prisoner group. Second-generation prisoners self-reported more anger and prison violence and demonstrated a greater presence of institutional rule breaking in comparison to first-generation prisoners. Results were maintained after statistical control for the high rates of adversities in childhood. Post hoc analysis revealed differences on adjustment variables between first-generation prisoners and individuals with a mother incarcerated or with both parents incarcerated, suggesting the pronounced impact of maternal incarceration on long-term well-being. Results indicate that the negative effects of parental incarceration are evident within the prison community and have a significant relationship to inmates’ adjustment while incarcerated.