Many women in detention are mothers and often the sole caregivers of their children. Italy, as most European countries, allows mothers to keep their children with them in detention, with the aim of preserving the fundamental bond between mother and child. Since prison does not seem to provide a good environment for the child’s growth, there are different alternative residential solutions, such as Group Homes. The aim of this preliminary study was to explore the differences between mothers living in detention through alternative measures with their children and mothers who are not detained regarding parenting stress, child behavior from the parent’s perspective, and maternal attachment. Twelve mothers were enrolled in this study, divided equally between the detained and the control groups. Both groups’ participants completed a three-questionnaire battery in order to assess parenting stress, child’s behavior, and maternal attachment. The analyses of variance showed significant differences between the two groups, with the detained group reporting higher scores than the control group in almost all the subscales of parenting stress. The results highlighted that imprisoned mothers might experience more stress than the general population. There is a need to design intervention programs to support parenting in detention.