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The goals of the study were to examine whether (a) risky behaviors precede depressive symptoms or, conversely, depressive symptoms predict risky behavior engagement; (b) gender moderates the relationship between risky behavior engagement and depressive symptoms; and (c) perceived control strengthens the association between risky behavior engagement and depressive symptoms. At Time 1, 118 adolescents completed self-report measures assessing perceived control, risky behavior engagement, and depressive symptoms. Follow-up assessments occurred every 6 weeks (Times 2-5), and participants completed measures assessing risky behavior engagement and depressive symptoms. Results indicated that neither risky behavior engagement nor depressive symptoms emerged as main effects for the sample as a whole. When examining the relationship between depressive symptoms and risky behavior engagement as a function of gender, boys', but not girls', risky behavior engagement predicted higher levels of depressive symptoms. Irrespective of whether we examined boys or girls, depressive symptoms did not predict risky behavior engagement. With regards to the role of cognitive vulnerability, adolescents with lower levels of perceived control reported higher levels of depressive symptoms following risky behavior engagement. These findings suggest that both gender and cognitive vulnerability factors may potentiate the relationship between risky behavior engagement and subsequent depressive symptoms.