This study examined whether DHEA and its ratio to cortisol moderated risk for psychopathology among incarcerated youth exposed to childhood maltreatment. Resistance to stress-related psychopathology under adversity was also examined in relation to callous-unemotional (CU) traits, a personality construct characterized by resistance to pathological anxiety and blunted reactivity to threatening stimuli. Participants were 201 ethnically heterogeneous (41.8% White, 35.3% Black, 17.2% Hispanic) adolescent boys (M age = 16.75, SD = 1.15 years) incarcerated in a juvenile detention facility in the South Eastern United States who provided four afternoon saliva samples (later assayed for DHEA and cortisol) and completed self-report questionnaires. Results indicated that childhood maltreatment was associated with greater internalizing problems at lower DHEA concentrations and at higher cortisol-to-DHEA ratios. Conversely, higher DHEA levels and lower cortisol-to-DHEA ratios were associated with greater CU traits, irrespective of maltreatment exposure. CU traits did not attenuate levels of psychopathology in maltreated youth. Findings inform biosocial models of how exposure to parental maltreatment in early life contributes to risk and resilience through mechanisms associated with adaptive environmentally sensitive biological systems and processes.