In 2018, through the Criminal Justice Investment Initiative, the Osborne Association launched Harlem FamilyWorks (HFW), an intergenerational enrichment, leadership, and healthy relationship program designed to serve youth, young adults, adults, and families impacted by the criminal legal system. This report presents the findings of the Urban Institute’s evaluation of the program, recommendations for how it can strengthen and enhance program operations, and implications other practitioners can consider when implementing similar programs for families impacted by the criminal legal system. From February 2018 to March 2021, HFW served 246 participants in the eligible age range from Central/West Harlem neighborhoods (the neighborhoods of focus), and it upheld the Criminal Justice Investment Initiative vision to address factors at the neighborhood level. Despite challenges with program start-up and the impact of the COVID-19 pandemic, participants, HFW staff, and community partners overwhelmingly reported positive experiences with the program. Participants also reported the program offered a safe space to share their legal system experiences, provided support from staff and other participants, and helped strengthen family relationships.