Aim <p>We tested an empirical model that describes contemporary risk-taking psychometrically on an indicator of psychosomatic symptoms in adolescents to determine the efficacy of newly developed scales and to identify contemporary behaviours that cluster together.</p> Subject and methods <p>Contemporary risk-taking is associated with negative health outcomes, especially when adolescents engage in multiple risk behaviours simultaneously. Validated measures that accurately reflect adolescent engagement in contemporary risks are needed for surveillance. The study base was the ninth cycle (2022–2023) of the Canadian Health Behaviour in School-aged Children (HBSC) study (<i>n</i> = 6799). Descriptive analyses were conducted, followed by structural equation modelling (SEM) to test the proposed relationship, both overall and by sex.</p> Results <p>The SEM illustrated that higher engagement in adolescent contemporary risk-taking was associated with an increase in psychosomatic symptoms, with an excellent psychometric fit (comparative fit index [CFI] = 0.98, Tucker–Lewis Index [TLI] = 0.98, root mean square error of approximation [RMSEA] = 0.05, standardized root mean residual [SRMR] = 0.07). From the three risk-taking clusters, higher engagement in online risk behaviours (β = 0.21; 95% CI [0.26, 0.16]) and contemporary substance use (β = 0.19, 95% CI [0.24, 0.15]) were most strongly associated with adolescents’ psychosomatic symptoms, followed by engagement in sexting (β = 0.10; 95% CI [0.14, 0.05]). Sex was not a moderator of these relationships.</p> Conclusion <p>Study findings demonstrate that contemporary risk-taking measures are consistently associated with indicators of psychosomatic symptoms. Additionally, contrary to prior evidence suggesting meaningful sex differences, the strength and direction of these associations were similar for both males and females. Understanding the changing landscape of risk-taking is essential to the conceptualization of adolescent health.</p>