This report explores the intergenerational effects of criminal records through five pillars of family well-being. The five pillars include: the impact of criminal records on income and the major obstacles parents with criminal records face in securing employment and receiving public assistance; the impact of mounting criminal justice debts and unaffordable child support arrears on families’ ability to save for the future; the impact on education, including the barriers parents with criminal records face to education and training opportunities that would increase their chances of findings well-paying jobs and better equip them to support their families; the impact on public as well as private housing that make family reunification difficult if not impossible; and financial and emotional stressors that often pose challenges to parents with criminal records in maintaining healthy relationships and family stability. The case is made for a two-generation approach to addressing barriers to opportunities associated with having a criminal record. The two-generation approach seeks to combat intergenerational poverty by boosting education, health and well-being, economic supports, and social capital for parents and their children. Policy recommendations are then offered to assist both parents with criminal records and their children. 132 references.