The Preschool Life Skills (PLS) program has a wealth of evidence demonstrating efficacy in remediating important social and learning-to-learn skill deficits in at-risk preschoolers. Those same skill deficits also are common in older children in foster or residential care, most of whom have experienced some sort of trauma or other adverse childhood events. This study sought to evaluate individualized PLS curricula for two boys with substantial trauma histories and demonstrate how the PLS program could be delivered within a trauma-informed framework. We delivered the program and evaluated skill acquisition in a one-to-one setting in a UK-based clinic, and asked caregivers to assess skills at home. Results showed that both boys acquired skills targeted in their individual curriculum, but maintenance was sometimes inconsistent. Social validity assessments suggested that both boys enjoyed the training but were less definitive about its overall benefits. Caregivers rated the program highly and reported skill improvements at home. We discuss the implications of these findings in terms of adapting the PLS program to children with trauma histories.