Agreement between adolescents, mothers, fathers, and teachers on adolescents’ personality traits was investigated in a longitudinal study. The targets for personality ratings were the adolescents who participated in the European Youth Heart Study in Estonia. There were 593 participants in the first wave and 480 participants in the follow-up study 3 years later. Adolescents’ self-reports as well as father, mother, and teacher ratings were collected using questionnaires to measure the five-factor model of personality. In both waves, inter-rater agreement was highest between mothers and fathers, was low to moderate for parent-self ratings, and was lowest for ratings between self and teacher, mother and teacher, and father and teacher. Test-retest correlations were moderate for parent and self-ratings but failed to reach statistical significance for three of the five teacher-rated traits, suggesting lower reliability of teacher ratings. Possible explanations for the low agreement between teachers and other judges are discussed.