Objective: the aim of the study was to examine the mediating role of stress in associations between online risky behavior and three factors, namely, real-life risky behaviors and information security awareness as risk factors, and life satisfaction as a protective factor. Method: participants were university students (N=883, 40.5% male, and 59.5% female) with an average age of M=21.93 years (SD=4.29). They filled out the Users’ Information Security Awareness Questionnaire, Youth self-reported delinquency and risk behaviors questionnaire, Life satisfaction scale and Perceived Stress Scale. Result: Mediational analysis revealed a mediating role of stress: stress had a partially mediating role in the association between real-life risky behaviors and online risky behavior, making the association stronger. However, stress had a fully mediating role in the association between life satisfaction and online risky behavior, that is, the association was non-significant in the presence of stress. Conclusions: Overall results indicate that stress experienced in real-life situations can be a trigger for online risky behavior in adolescents. Under stressed conditions, adolescents choose to focus on negative outcomes more frequently because they refocus their cognitive resources on emotion regulation and leave inhibitory processes necessary to prevent risky behaviors uncontrolled.