A parent’s history of maltreatment is a highly associated risk factor to the presence of actual maltreatment, particularly within the child protective services (CPS) clientele. Considering the lack of knowledge in terms of CPS’ quality, quantity, and effectiveness with intergenerational maltreating families, this study aims to analyse CPS workers’ perceptions about this question. They demonstrate obvious helplessness considering intervention needs to be intensive, stable, and long-term with these parents, but within a context where practitioners are overloaded, where there is no continuity of services, and where a relationship based on trust is hard to establish. A reflection on the CPS’ capacity to break the intergenerational transmission cycle, considering its legislative mandate, is undertaken.