We describe an evaluation of a prison-visiting program, Extended Visiting (EV), for incarcerated mothers and their children. Mothers (N = 24) and caregivers (N = 19) were interviewed regarding experiences with the program. Mothers identified benefits including maintaining a relationship with children, physical contact, motivation, privacy, peer support, and personal growth. Caregivers echoed mothers’ appreciation for the opportunity to maintain mother–child relationships and physical contact. Mothers identified barriers including desire for overnight visits and more age-appropriate activities. Caregivers perceived travel time and costs and children’s adverse reactions as barriers. When comparing EV to typical visiting, participants unanimously preferred EV.