© 2022 Michigan Association for Infant Mental Health.Anxiety problems are seen as early as 1–2 years of age. Among others, parenting and child temperament are considered as the most important factors affecting anxiety in early childhood. In the current study, the unique roles of parenting (maternal overprotectiveness and warmth) and temperament (behavioral inhibition and negative emotionality), parenting-temperament interactions, and mediating role of ambivalent attachment between behavioral inhibition and anxiety were investigated. One-hundred mother–child (18–36-month-old) dyads participated in this study. Children's anxiety and temperament were measured through mother-reported scales, attachment was measured by observation via home visits, and parenting dimensions were measured via both mother-reported scales and observation. The results revealed that behavioral inhibition and overprotectiveness were positively associated with toddlers’ anxiety, whereas there were no significant direct associations of negative emotionality and warmth with anxiety. However, the interaction between behavioral inhibition and warmth predicted toddler's anxiety; that is, if behaviorally inhibited children had mothers who were low on warmth, those children were more likely to exhibit anxiety symptoms compared to children with low behavioral inhibition, whereas anxiety levels did not change for children of warm mothers. Ambivalent attachment mediated the relationship between behavioral inhibition and anxiety. The nature of parent-child interactions is discussed based on toddlerhood anxiety.