Previous research has utilized naturalistic observations of parent-child interactions at bedtime to identify constellations of specific parenting behaviors and qualities that predict better infant nighttime sleep. Little work, however, has naturalistically examined associations between aspects of bedtime parenting and nighttime sleep among young children. The present study assessed observed parenting practices and sensitivity in the context of bedtime as predictors of 3-6-year-olds' sleep. Participants were 51 children (53% boys; 80% White, 18% biracial, 2% Black) and their families. Trained raters coded video recordings of bedtime for parenting practices (parental presence, contact, quiet activities; children's technology use) and sensitivity. Children's nighttime sleep (minutes, efficiency) was assessed across seven nights using actigraphy. Partial correlation analyses controlling for child and family demographics showed that more quiet activities, greater parenting sensitivity, and less child technology use at bedtime were associated with longer and more efficient sleep. There were also several significant interactions. Longer parental presence and contact at bedtime were associated with better sleep (minutes, efficiency) for children who experienced high but not low parenting sensitivity. Lower child technology use in combination with higher parental presence was also associated with longer and more efficient child sleep. The findings illuminate aspects of the bedtime context that may promote emotional security and reduce physiological and cognitive arousal in young children. These naturalistic observations may readily translate into intervention programming targeting improvement in young children's sleep. (PsycInfo Database Record (c) 2022 APA, all rights reserved).