ABSTRACT Frightening maternal behavior is linked to infant disorganization, which predicts child behavioral problems. We examined continuity in frightening maternal behavior across the first 2 years by developing a new measure of anomalous/frightening (AN/FR) behavior that incorporates changes in parent–child interactions as children acquire symbolic representation. Maternal AN/FR behavior in toddlerhood also was examined in relation to later internalizing and externalizing symptoms. First-time mothers (N = 125) completed the Adult Attachment Interview (AAI) prenatally, and mother–child dyads were observed interacting at 8 months, in Strange Situations at 12–15 months, and playing at 24 months. Teachers rated children’s behavior problems at 7 years. Mothers classified as Unresolved on the AAI displayed more Frightening (FR) behavior at 8 months. Mothers’ FR behavior predicted both attachment disorganization at 12–15 months and maternal AN/FR behavior at 24 months, which then predicted children’s internalizing symptoms at age 7. Infant disorganization was indirectly related to internalizing symptoms, mediated by maternal AN/FR behavior.