Structural and system theories propose that disruptions in family subsystem functioning increase risk for youth maladjustment. While there is growing evidence to support this proposition, studies that specifically focus on the larger family system remain relatively rare. Furthermore, the pathways that connect problems in family subsystem alliances to externalizing or internalizing problems in youth are as yet largely unexplored. This study examined youth emotional reactivity (anger and sadness) to family conflict as an indirect pathway of the association between family boundary disturbances and youth adjustment in a sample of two-parent families (N = 270). Observational coding was used to group families into Balanced, Dyadic, or Disengaged family alliance structures and to assess youth emotional reactivity, and parent-report was used to assess youth psychopathology. Structural equation modeling indicated both anger and sadness served as indirect pathways through which family boundary disturbances are linked with youth adjustment. In addition, gender was tested as a moderator and important gender differences were found. Specifically, boys were directly impacted by dyadic disturbances while girls were directly impacted by family disengagement. The findings help target goals for intervention and indicate that worthwhile objectives may include realigning family subsystem boundaries, changing family communication patterns, and improving affective coping skills for youth.