This study examined the relations between hassles and internalizing and externalizing symptoms across 4 years in adolescents who varied with regard to their risk for psychopathology. The sample comprised 240 adolescents assessed in 6th, 7th, 8th, and 9th grades regarding their level of peer and academic hassles and internalizing and externalizing symptoms. Structural equation modeling was used to construct latent variables of hassles and internalizing and externalizing syndromes. Results varied by informant about the teens' symptoms. For adolescent report, the stress exposure model fit the data best for internalizing syndromes; that is, higher levels of stressors predicted significantly higher levels of self-reported symptoms 1 year later. For mother report of adolescents' symptoms, the stress generation model fit the data best for both internalizing and externalizing syndromes; that is, higher levels of adolescents' internalizing and externalizing symptoms, as reported by their mothers, significantly predicted higher levels of hassles 1 year later.