This study evaluated the family-inclusive case management component of the Chicago-based Safer Return program, which engages family members in service provision to former prisoners. Using qualitative and quantitative data, the research focused on the associations between family support and family members’ and formerly incarcerated persons’ short-term outcomes. The research found that family members have strong and positive relationships with their formerly incarcerated relatives. However, engaging families in the reentry process directly can be challenging because incarcerated persons are reticent to nominate family members and/or family members are unwilling or unable to participate in their family member’s reentry program.