Research indicates that insecurely-attached adolescents are at risk for depression, but little is known about factors that may influence or explain this vulnerability. The present study focuses on close relationships during adolescence and their association with depression. Specifically, the objectives were to investigate (1) the role of working models of specific attachment figures (i.e., mother, father, best friend, and romantic partner) in the prediction of depression; and (2) the existence of target-specific pathways to depression following relational stress. It was expected that the paths to depression would differ depending on the attachment figure under consideration. A total of 134 adolescents (n = 88 girls; M age = 16.95 years; SD = 0.74) completed attachment questionnaires, a depression inventory, and a computer task consisting of hypothetical interpersonal vignettes and questions. Insecure attachment relationships with romantic partner, and for girls only, with mother, were uniquely predictive of depression. Insecurely-attached adolescents' tendency to make negative attributions in response to stresses fully mediated the attachment-depression association. These adolescents were found to ruminate when confronted with stresses involving romantic partner, which was also associated with depression. Results underscore the link between attachment, negative attributions, and depression.