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Despite the great number of children affected by anxiety and depression, developmental trajectories of internalizing disorders are not well understood. The current study applied a group-based modeling approach to examine the interplay between the temperamental trait of negative emotionality and parenting on internalizing symptoms from early childhood to adolescence. Using data from the National Institute of Child Health and Human Development Study of Early Child Care and Youth Development (N = 881), analyses revealed that a four-group model best characterized trajectories of internalizing symptoms from the age of 4.5 to the age of 15. Interestingly, children with high negative emotionality were more likely to belong to groups with elevated levels of internalizing symptoms if their mothers exhibited high warmth/sensitivity. Our findings add to the understanding of developmental pathways of internalizing problems from early childhood to adolescence by suggesting that certain combinations of temperament and parenting may increase youth's propensity to develop internalizing problems.