For many years, clinical case studies that have focused on the intergenerational effects of Holocaust trauma have indicated that second-generation Holocaust survivors (SGHSs) often face relational challenges in their intimate relationships. The relational attitudes of SGHSs during childhood, as well as during adulthood, have been studied. However, only in recent years has this cohort entered the “aging adult” group. In this study, we hypothesized that well-being among Israeli aging SGHSs would be associated with parentification and with specific relational attitudes toward their adult offspring. We examined whether parentification, sense of relational entitlement, pathological concern, and authenticity in relationships mediated the association between family background and well-being. A total of 329 participants (60% SGHSs; 19% men) completed questionnaires tapping retrospective accounts of parentification during childhood, inflated and restricted senses of entitlement, pathological concern, relational authenticity, and subjective well-being. Aging SGHSs reported higher levels of parentification, inflated sense of entitlement toward offspring, pathological concern, lower levels of authenticity, and subjective well-being. The association between family background and subjective well-being was mediated by parentification, inflated sense of relational entitlement, pathological concern, and authenticity. Findings suggest that especially for aging SGHSs, childhood parentification takes a heavy toll on their sense of well-being via the hindering of a balanced sense of relational entitlement and concern and the authentic expression of self.