This correlational study involved observations of 144 separate diapering cycles by 31 caregivers with 74 infants and toddlers in 30 infant and toddler classrooms in a U.S. Midwest city. Based on these observations, caregiver responsiveness was found to be significantly related to both child involvement and child well-being. Another feature of caregivers’ behavior, caregiver encouragement, was significantly associated with child well-being, but not child involvement. The study results suggest that caregivers’ behaviors, specifically responsiveness and encouragement, during diapering are vital proximal processes in the moment-to-moment interactions between a caregiver and child. Thus, responsiveness and encouragement in care routines should be emphasized in infant care settings and be a focus for caregiver professional development, including pre- and in-service training. (author abstract)