The intergenerational transmission of attachment insecurity was examined in a community sample of 300 participants consisting of 100 three-generation triads of women. It was hypothesized that personality vulnerabilities mediate the association between attachment insecurity and depression within each generation. Findings show significant intergenerational congruence of trait vulnerabilities and attachment styles. Moreover, the second generation's attachment dimensions and personality vulnerabilities were found to mediate the association between first- and third-generation scores on attachment and vulnerability variables. Findings supported the following hypothesized within- and between-generation paths: Within generations, self-criticism was found to mediate the association between attachment insecurity and depression; between generations, depression, but not self-criticism, mediated the association between assessments of attachment insecurity in mothers and their daughters. This study constitutes a first approach to the delineation of the role played by self-criticism in the association between negative models of the self and depression across generations.