Emotions and behaviors observed during challenging tasks are hypothesized to be valuable indicators of young children's motivation, the assessment of which may be particularly important for children at risk for school failure. The current study demonstrated reliability and concurrent validity of a new observational assessment of motivation in young children. Head Start graduates completed challenging puzzle and trivia tasks during their kindergarten year. Children's emotion expression and task engagement were assessed based on their observed facial and verbal expressions and behavioral cues. Hierarchical regression analyses revealed that observed persistence and shame predicted teacher ratings of children's academic achievement, whereas interest, anxiety, pride, shame, and persistence predicted children's social skills and learning-related behaviors. Children's emotional and behavioral responses to challenge thus appeared to be important indicators of school success. Observation of such responses may be a useful and valid alternative to self-report measures of motivation at this age. (Contains 7 tables and 1 figure.)