We found mothers’ history of depression and symptoms of depression among their adolescent children were both associated with the type of events that mothers made adolescents feel guilty about and with the mothers’ reactions to those events. Adolescents (20 male, 23 female) described incidents in which their mothers made them feel guilty and what happened afterward. Offspring of mothers with (versus without) a history of depression more often reported guilt when not at fault and over failing to meet maternal needs; reactions did not resolve matters and involved unregulated maternal emotions. Adolescents of mothers without a depression history more often felt guilty about specific events (e.g., breaking rules, bad grades) and reactions resulted in closure (through discipline, apologies, or forgiveness). Adolescents’ depressive symptoms were more severe when incidents were unresolved and involved maternal emotions and less severe when incidents were specific. In addition, maternal use of self-serving forms of guilt induction related to adolescent and parent depression.