An intergenerational study examined mothers' insecure attachment style using the Attachment Style Interview (ASI; Bifulco et al., 2002a) in relation to her history of partner relationships, her parenting competence, and depression or anxiety disorder in her offspring. The sample comprised 146 high-risk, mother-adolescent offspring pairs in London, who were recruited on the basis of the mothers' psychosocial vulnerability for depression. Retrospective, biographical, and clinical interviews were undertaken independently with mother and offspring. A path model was developed, which showed that mothers' insecure attachment style had no direct link to either recalled child neglect/abuse or currently assessed disorder in their adolescent and young adult offspring. The connections appeared to be indirect, through the quality of relationships in the family system: mothers' insecure attachment and their partners' problem behavior accounted for variance in mothers' incompetent parenting as rated by interviewers. These variables predicted her neglect/abuse of the child, which was the only variable directly associated with internalizing disorder in her offspring. Mother's lifetime depression did not add to the model. It is argued that an ecological approach (emphasizing social adversity and different role domains) and a lifespan approach (emphasizing a history of adverse relationships a different life stages) is important in understanding the mechanisms by which parental insecure attachment style influences transmission of risk to the next generation.