Using data from three waves of a large Canadian data set, this research examined the relationship between middle-childhood trajectories of family dysfunction and indirect aggression. The authors applied family systems, developmental psychopathology, and life-course conceptualizations to meet this objective. The data analytic strategy used separate multivariate logits to examine this relationship, with and without the extent to which other possible explanations (acting as control variables) predict belonging to the highest family dysfunction trajectory. These included marital transition, socioeconomic status, family size, and depressive symptoms experienced by the adult most knowledgeable about the child (mostly mothers). The authors also explored possible interactions between indirect aggression and these explanatory variables. Supporting their hypothesis for both boys and girls, prolonged-duration high doses of family dysfunction were associated with the most extreme developmental trajectories of indirect aggression during middle childhood. Results showed gender specificity with respect to the influence of the explanatory variables on family dysfunction. For girls, the link between family dysfunction and indirect aggression persisted above and beyond such contextual influences. For boys, the relationship became unimportant once contextual factors were taken into account.