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This case study analyzes descriptions given by a 21-year-old mother of her 3-year-old son as illustrations of characteristics consistent with attachment disorganization. Descriptions are taken from two sources: the Insightfulness Assessment, an attachment-based interview designed to assess qualities of caregivers' internal working models of their children, and group sessions of an attachment-based parenting intervention, the Circle of Security. Relevant discourse qualities identified include emotional disengagement; contradictory and unintegrated positive and negative perceptions; intrusive, painful memories from her past; blurring of identity boundaries; and feelings of burden mixed with fears of his emotional estrangement from her. Changes in discourse qualities are also identified that appear consistent with changes in attachment security assessed for both mother and child before and after the mother's participation in the intervention. Understanding of attachment disorganization and associated discourse characteristics is important because of its prevalence among maltreating parents and the life-span developmental consequences with which it is associated.