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.