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This investigation evaluated a theoretically specified model of associations among mothers’ history of child sexual abuse (CSA), a helpless state of mind (SOM) with regard to the mother–child relationship, and increased behavior problems in the next generation. Moreover, we evaluated the moderating influence of child gender on predicted relations between mothers’ CSA severity and helpless SOM (i.e., moderated mediation). Participants were 225 biological mother–preschooler dyads (48% female; 46.4% Latinx) drawn from an ongoing, longitudinal study of representation and regulation in child development. Mothers’ history of CSA was assessed when their children were 4 years old and emerged as a prominent risk factor in this diverse, high-risk community sample with 40% of mothers reporting contact-based sexual abuse prior to age 18. Mediation analyses revealed a significant indirect pathway from a continuous rating of mothers’ CSA severity to increased externalizing behavior problems from ages 4 to 8 in the next generation via mothers’ helpless SOM at age 6. Further, this indirect path was significant for mother–daughter dyads, but not for mother–son dyads. This investigation contributes to the neophyte literature on intergenerational CSA effects by revealing the impact of a mother’s CSA history on her SOM regarding the mother–child relationship, particularly when parenting daughters. Clinical interventions that enhance survivors’ awareness of and reflection on their SOM regarding the parent–child relationship may attenuate intergenerational CSA effects on child adaptation. [ABSTRACT FROM AUTHOR]