This article presents an attachment theory and research-based perspective on the utility of assessing qualities of mental representations as indexes of change in an adoption context. The article reviews findings from a large, longitudinal and intergenerational study of attachment relationships of previously maltreated children who were adopted in latency. An attachment perspective provides a secure base from which to explore how old objects were carried into these new relationships, by both adoptive parents and the children recently placed with them. The study has the potential to inform a wider area of interest, namely to add to our knowledge base concerning the assessment of mental representations in both children and adults. The possibility to provide empirical evidence for intergenerational links and changes in representations over time in relation to a new environment is helpful, especially if we can chart relationships that can facilitate or inhibit the emergence of trust, growth, and the development of corresponding representations.