Drug use among young people is increasing in Africa. To prevent drug use, it is essential to understand the motivations, environments, and characteristics of users. Although there are established risk factors for drug use, little is known about the reasons why adolescents and young people take drugs. This study investigated the reasons given by a sample of secondary school pupils for using drugs and other substances, specifically, how adolescents circumvent the restrictive and prohibitive policy regime and rationalize and account for drug use. This study used a cross-sectional mixed-methods design. For quantitative data, descriptive and regression analyses were run, and for qualitative data, thematic analysis was used. About 13 per cent (n=41) met criteria for moderate to severe drug use. Coping (Mean = 4.13, SD 0.89), social (Mean = 3.71, SD 0.97), and enhancement (Mean = 3.09, SD 0.92) motives were highly endorsed as motives for drug use. The extent to which motives predicted drug use ranged from β = 0.55 (95% CI: 0.39, 0.72) for coping to β = 0.18 (95% CI: 0.08, 0.28) for expansion motives. Students employed ingenious and frequently risky ways to circumvent the rigorous and prohibitive regulatory regimes governing drug use in schools. Academic stress, limited recreational activities, poor stress management, peer influence, poor adult supervision and dysfunctional family backgrounds, all interrelate in complex ways with motives, contexts, and student characteristics to create a conducive environment for the rationalisation, medicalisation, and veneration of drug use. Further research on contexts, motives and characteristics of adolescents that shape drug use is needed.