This longitudinal study examined links between disorganization and atypical maternal behavior at 12 and 24 months in 71 adolescent mother–child dyads. Organized attachment and maternal not disrupted behavior were more stable than disorganization and disrupted behavior, respectively. At both ages, disorganization and maternal disrupted behavior were significantly correlated. Change in atypical maternal behavior predicted change in disorganization across time. The results provide substantial support for extant theories linking anomalous maternal behavior to the development of disorganized attachment. The Interesting-but-Scary paradigm, introduced in this study, promises to be a useful tool for assessing attachment and maternal behavior in toddlerhood.