Behavioural adjustment is critical for children's school readiness. This study used data from a nationally representative sample of children from the Early Childhood Longitudinal Study-Birth Cohort. We examined the effects of interactions between children's negative emotionality, maternal sensitivity and preschool teacher sensitivity on children's kindergarten internalizing and externalizing behaviours. Parent report of children's negative emotionality and observations of maternal sensitivity were obtained at age 2?years, teacher sensitivity was observed in preschool and teacher report of children's behaviour problems was obtained in kindergarten. Negative emotionality moderated links between maternal sensitivity, teacher sensitivity and children's internalizing behaviours. For children high in negativity, maternal sensitivity was positively associated with internalizing behaviour in the context of low teacher sensitivity, whereas for children low in negativity, maternal sensitivity was negatively associated with internalizing behaviour. For children high or low in negativity, internalizing behaviour was comparable when teacher sensitivity was high regardless of maternal sensitivity. Maternal sensitivity and teacher sensitivity interacted to predict externalizing behaviour regardless of child negativity. Children who experienced high teacher sensitivity displayed comparable externalizing behaviour regardless of maternal sensitivity. When children experienced low teacher sensitivity, maternal sensitivity was negatively associated with externalizing behaviour. Interactions between child characteristics and caregiving across developmental contexts are discussed.