Parental incarceration can be devastating for families. Children may experience difficulties, and the stress on caregivers who take on unexpected childrearing is high. We implemented and evaluated a family-level intervention with caregivers and children experiencing parental (typically maternal) incarceration, in a community setting. We partnered with a community-based organization serving families with an incarcerated parent to conduct a pilot trial of the Strengthening Families Program (SFP). Process evaluation indicated high implementation fidelity, satisfaction, engagement, and attendance. Outcome evaluation results indicated positive changes in family-level functioning, caregivers’ positive parenting, and caregiver depression symptoms from pre- to post-intervention, with some changes retained at follow-up 4 months later. Implications for preventive interventions with children of incarcerated parents, and their caregivers, are discussed.