This inquiry examines the relationship between caregiver confirmation and children’s attachment security during the transition to kindergarten. Caregiver-child dyads (N = 50) read a story about the transition to school, caregivers responded to hypothetical child statements of concern concerning starting school, and caregivers completed the Attachment Q-Sort measure (Waters, 1995). Caregivers’ behaviors during portions of the storybook task and their written responses to hypothetical child statements of concern were coded for verbal and nonverbal “confirmation as acceptance” and verbal “confirmation as challenge.” Children’s attachment security scores were created from the Attachment Q-Sort. Caregivers’ level of education moderated the association between caregiver confirmation as verbal and nonverbal acceptance and children’s attachment security such that there was a positive association between confirmation and attachment security mainly for caregivers with low levels of formal education. Implications for the literatures on confirmation, attachment, and the transition to school are debated.