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This study uses General Strain Theory (GST) and studies of the stress process to describe and examine one potential pathway of the escalation and de-escalation of illicit drug use from adolescence and young adulthood. In particular, the time-varying consequences for drug use of persistent or increasing levels of strain are addressed using data from the Family Health Study, an eight-year longitudinal data set (n = 840). The results indicate that there is a positive association between experiencing one type of strain—stressful life events—and involvement in illicit drug use during this period of the life-course. However, the impact of stressful life events on this behavior is diminished among young adults. Moreover, drug using peers reduce the age-specific effects of stressful life events, thus suggesting that peers play a central role in the association between strain and drug use. Implications of the results for theory and policy are discussed.