This investigation originated from a pilot survey of 261 state prison inmates, aged 45 to 82, in Oklahoma. Logistic regression analyses were computed to assess the relationship of sociodemographic characteristics, physical and mental health, and lifestyle behaviors to comorbid health impairment. (odds ratio (OR) = 1.41, 95% confidence interval (CI) [1.13, 1.77]), smoking (OR = 2.82, 95% CI [1.10, 7.30]), and church attendance (OR = 1.23, 95% CI [1.00, 1.50]) were associated with increased odds of comorbid health impairment. Perceived health (OR = 0.38, 95% CI [0.23, 0.66]), mobility (OR = 0.25, 95% CI [0.09, 0.70]), and physical exercise (OR = 0.56, 95% CI [0.35, 0.88]), were associated with reduced odds of comorbid health impairment. Education, smoking, and church attendance represent key indicators of comorbid health impairment, whereas perceived health, mobility, and physical exercise are more likely to reduce multiple health impairments.