The present study was designed to examine the relationship between characteristics of mothers and their toddler's insecure and dependent behavior. The authors studied 254 2-year-old toddlers and their mothers via a structured questionnaire administered to the mothers in their homes. The extent to which insecure and dependent behavior is related to the domains of maternal child rearing, maternal personality traits, parental marital relations, and maternal drug use was assessed. Using Pearson correlations and hierarchical multiple regression analyses, the authors found that the maternal child-rearing and maternal personality domains have a direct effect on the toddlers' insecure and dependent behavior. The maternal child-rearing domain also served as a mediator for the domains of the maternal personality attributes, parents' marital relations, and maternal drug use. There also was evidence suggesting an indirect effect of maternal personality attributes on the toddlers' insecure and dependent behavior, which is mediated by the domain of maternal child-rearing practices. Implications for the prevention of insecure and dependent behavior in toddlers are discussed.