The present research examines how preschoolers' attachment representations relate to maternal psychosocial problems, differentiating by gender. One hundred and thirty-seven mothers along with their 36-49 month old children (51 female) who attend child-care centers were evaluated. Trained researchers administered interviews and collected self-reported measures of family risk factors, depressive symptoms and parenting stress from each mother. The children were assessed using the Attachment Story Completion Task and the CCH Q-sort coding system. Results show that children of both genders scored higher in security than in other dimensions and girls showed higher security and lower insecurity levels than boys. General maternal stress levels relate directly to girls' and indirectly to boys' insecurity levels. Regarding family risk factors, it seems that environment instability, along with the lack of routines, low parental caregiving capacities and conflictive family interactions interfere negatively with the development of a secure internal working model in both girls and boys. © 2013 Elsevier GmbH.