The paper presents a developmental and dynamic multitheoretical overview of many dimensions of attachment-related processes activated under the conditions of maternal depression. The clinical vignette (from the analytic practice of Eva D. Papiasvili) of reconstructive anaytic work with an adult patient illustrates the profound impact of maternal depression on precocious early differentiation between the attachment styles, of the depressed parent and the substitute caregiver, at the root of early “counterdependent” self-sufficiency. Through reconstructive interpretive work, first with enactments and then dreams, pertaining to not-remembered, represented, or symbolized events of earliest infancy, the patient is able to make a series of developmentally transformative symbolic leaps, restoring the capacity for intimacy, hope, trust, and pleasure. This breaks the intergenerational mother–daughter transmission of postpartum depression and related problematic attachment.