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The current study tested the diathesis-stress component of the hopelessness theory (HT) in a sample of youth using (1) a weakest link approach towards operationalizing cognitive vulnerability (e.g. a child's degree of vulnerability is determined by his/her most depressogenic inferential style; DIS) and (2) an idiographic approach towards operationalizing high stress (e.g. high stress is when a child is experiencing a level of stress that is higher than his/her own average level of stress). We also examined whether the association between within-subject fluctuations in hassles and depressive symptoms in cognitively vulnerable youth was moderated by absolute stress levels (the between-subject effect of stress).A multi-wave longitudinal design was used to examine whether the association between within-subject fluctuations in hassles and depressive symptoms was moderated by a depressogenic weakest link.At Time 1, 140 children (between 6 and 14 years of age) of parents with a history of major depressive episodes completed measures assessing DISs and depressive symptoms. Every 6 weeks, for the subsequent year, children completed measures assessing depressive symptoms and hassles.The results of hierarchical linear modelling analyses indicated that a depressogenic weakest link was associated with greater elevations in depressive symptoms following elevations in hassles in girls but not in boys.Results provide partial support for the applicability of the diathesis-stress component of the HT to youth. Integration of the current findings with those obtained in past research examining the diathesis-stress component of the hopelessness theory in youth suggests the utilization of an idiographic approach to examining vulnerability-stress theories may potentially lead to an increased understanding of gender differences in depression.