This study tested Bowlby and Ainsworth’s hypothesis that a hierarchy of caregivers exists whereby infants prefer one caregiver over another when distressed. We examined parent gender (mother vs. father), primary caregiver status (defined as the parent who spent most time with the infant and performed most of the caregiving tasks), and role of toddlers’ history of attachment security with each parent, as predictors of toddlers’ preference for a particular caregiver when the toddlers are distressed and when they are content. Infants’ attachment security with each parent was assessed at 12–15 months. At 24 months, mother–child and father–child interactions were observed in triadic (mother, father, toddler) home interactions. When distressed, regardless of the security of their attachment to each parent, toddlers more often interacted with the primary caregiver. When content, toddlers did not show this preference. As expected, toddlers’ recovery from distress was predicted by their security of attachment with the parent whom they approached when distressed.