The present study examined the relationships between childhood attachment, adult attachment, self-esteem, and psychological distress; specifically, it investigated the multiple mediating roles of self-esteem and adult attachment on the association between childhood attachment and psychological distress. Using 1,708 adult participants, a multiple-mediator model analysis following bootstrapping procedures was conducted in order to investigate the mechanisms among childhood and adult attachment, self-esteem, and psychological distress. As hypothesized, childhood attachment was significantly associated with self-esteem, adult attachment, and psychological distress. Self-esteem was found to be a significant mediator for the relationship between childhood attachment and adult attachment. In addition, adult attachment significantly mediated the relationship between self-esteem and psychological distress. The results provide insight on counseling interventions to increase adults’ self-esteem and attachment security, with efforts to decrease the negative impact of insecure childhood attachment on later psychological distress.