Data are sparse regarding the impact of psychosocial work stress on the health and well-being of aging workers, even for employees working in high-stress occupations, such as law enforcement. To improve our understanding of this issue in older workers, we assessed and characterized work stress, coping strategies, and stress-related health outcomes in a sample of police officers aged 50 years and older (n = 105). The most important risk factors associated with officers’ perceived work stress were maladaptive coping behaviors (eg, excessive drinking or problem gambling) (odds ratio [OR], 4.95; 95% confidence interval [CI], 2.11 to 11.6) and exposure to critical incidents (eg, shootings) (OR, 3.84; 95% CI, 1.71 to 8.65). In turn, perceived work stress was significantly associated with anxiety (OR, 6.84; 95% CI, 2.81 to 16.65), depression (OR, 9.27; 95% CI, 3.81 to 22.54), somatization (OR, 5.74; 95% CI, 2.47 to 13.33), posttraumatic stress symptoms (OR, 2.89; 95% CI, 1.29 to 6.47), symptoms of “burnout” (OR, 5.93; 95% CI, 2.54 to 13.86), chronic back pain (OR, = 3.55; 95% CI, 1.57 to 8.06), alcohol abuse (OR, 3.24; 95% CI, 1.45 to 7.22), and inappropriately aggressive behavior (OR, 4.00; 95% CI, 1.34 to 11.88). These data suggest that older workers in high-stress jobs may be at increased risk for work stress–related health problems, especially if they rely on risky health behaviors to cope with stress. Given the size of the rapidly aging US workforce and the likelihood that many are employed in high-stress jobs, interventions are urgently needed to address this emerging public health issue.