It is hypothesized that hypothalamic-pituitary-adrenal and hypothalamic-pituitary-gonadal axes function together to maintain adaptive functioning during stressful situations differently in adolescence than the characteristic inverse relations found in adulthood. We examined within-person correlated changes (coupling) in cortisol, DHEA and testosterone in response to parent-adolescent conflict discussion, social performance, and venipuncture paradigms. Data are derived from two samples of boys and girls from the Northeastern US (213 adolescents aged 11-16, M=13.7, SD=1.5 years; 108 adolescents aged 9-14, M=11.99, SD=1.55) using different biological sampling vehicles (saliva and blood). Results consistently show that across samples, vehicles, and contexts, cortisol and DHEA and cortisol and testosterone are positively coupled in response to environmental stimuli. Findings underscore the importance of considering the effects of multiple hormones together in order to further our understanding of the biological underpinnings of behavior, especially during adolescence, as adolescence is a developmental transition period that may be qualitatively different from adulthood in terms of hormone functioning.