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Cross-sectional studies have shown that both stressors and personality vulnerability are risk factors for adolescent problematic Internet use (PIU). However, little is known about how both categories of factors in combination may contribute to the longitudinal development of PIU among adolescents. The aims of this study were to document the developmental pattern of PIU among adolescents and to examine how stressful life events and the Big Five personality traits jointly affect the development of PIU. We tested three competing models: the additive, diathesis-stress, and social push models. A total of 1,365 adolescents participated in a 3-year longitudinal study. Hierarchical linear modeling indicated that PIU among adolescents increased over the 3-year period. After controlling for demographics and the Big Five personality traits, stressful life events (a time-varying predictor) were positively correlated with the initial level of, and the rate of change in, PIU. After controlling for demographics and stressful life events, four of the time-invariant Big Five personality dimensions had a significant effect on the initial level of PIU. Low Agreeableness, low Conscientiousness, high Openness, and high Neuroticism were positively associated with high initial PIU. In addition, Extraversion was negatively associated with and Conscientiousness was positively associated with the rate of change in PIU. The interaction effect between the personality and stressors was not significant. Therefore, the data provided support for the additive model, indicating that stressful life events and personality dimensions each make a unique contribution to PIU and that both should be considered in the prevention of adolescent PIU.