In role reversal a child takes an inappropriate parental, spousal, or peer role with the caregiver. The study assessed attachment disorganization with mother in infancy in the Strange Situation (Ainsworth, Blehar, Waters, Wall, 1978) and role reversal at 2 years old in videotaped mother-child interactions. By closely observing role reversal at this early age, results fill in the picture concerning the link between disorganized infant-mother attachment and controlling role reversal at 6 years old (Main Cassidy, 1988; Main, Kaplan, Cassidy, 1985). As hypothesized, infant-mother disorganization significantly predicted mother-toddler role reversal. The study also deepened research that predicted role reversal from parent Adult Attachment Interview (AAI) role reversal assessed before the child was born (Macfie, McElwain, Houts, Cox, 2005). As hypothesized, mother AAI role reversal with her mother in childhood significantly predicted mother-toddler role reversal over and above infant-mother disorganization. Results are discussed within a developmental psychopathology framework including opportunities for developmentally sensitive interventions.