Despite evidence of some intergenerational continuity of maltreatment, a notable proportion of parents maltreated in childhood do not perpetuate the cycle of maltreatment. The aim of this study was to identify factors that would distinguish mother–child dyads where intergenerational continuity was present from dyads characterized by intergenerational discontinuity. The sample included 193 children and their mothers, drawn from two populations: 74 maltreated children recruited through Child Protection Services and 119 nonmaltreated children recruited among low-income families. Factors investigated included maternal childhood maltreatment, psychological functioning, and family ecology. Compared to maltreated mothers who broke the cycle of maltreatment, those who perpetuated the cycle were more likely to have experienced childhood physical neglect and multitype maltreatment, and to experience sociodemographic risk, intimate partner violence, and lack of family support. Compared to nonmaltreated mothers who maintained a nonmaltreating child-rearing environment: (a) maltreated mothers who broke the cycle were more likely to experience residential instability and lack of family support, and (b) nonmaltreated mothers whose child was maltreated were more likely to experience sociodemographic risk and lack of family support. Maternal psychological functioning did not discriminate maltreatment groups. Lending empirical support to a diathesis-stress model of poor parenting, these findings suggest that family-ecology related stress, but not maternal psychological difficulties, may create additional burden that will precipitate the risk of maltreatment intergenerational continuity.