Employing a quasi-experimental design, this study explored the long-term effects of different childrearing ecological contexts. Participants were 131 adolescents (aged 16 – 18) from four groups: some who lived in a city, some from a kibbutz familial setting, some from a kibbutz communal setting, and a transitional group that included adolescents raised in a communal setting as young children who moved to a familial sleeping arrangement before the age of six. Adolescents' state of mind with regard to attachment and representations regarding separation were examined. Participants were administered the Adult Attachment Interview, the Separation Anxiety Test, and background questionnaires. The group raised in a communal setting in the kibbutz showed a higher incidence of nonautonomous attachment representations and less competent coping with imagined separations than did the other groups. By contrast, the transitional group was comparable to the city and the kibbutz familial groups. These results are discussed in light of the plasticity and adaptability of children to changed circumstances.