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Occupational stress is a pervasive problem that is relevant across the world. Stress, in combination with occupational hazards, may pose additive risks for health and wellbeing. This chapter discusses the influence of physical and psychosocial stressors on basal cortisol regulation as associated with higher-risk occupational duties among two subspecialties of police officers (frontline and special tactical unit officers). Results reveal significant differences in dysregulated cortisol awakening response associated with the higher risk duties among special tactical unit officers. In contrast, frontline officers with a lower objective occupational risk profiles report higher subjective stress levels. Dysregulated or maladaptive cortisol levels are associated with increased health risk. Thus, individuals working in high stress occupations with elevated cortisol profiles may be at increased risk of chronic health conditions. Results suggest that considering both objective physiological markers and subjective reports of stress are dually important aspects in designing interventions for police officers of differing subspecialties.