The proliferation of lotteries and casinos has led to increased participation in gambling. Older adults who have opportunities to gamble may be vulnerable to gambling problems, and incarcerated older adults may be the most vulnerable. Furthermore, research has linked decreased health to gambling problems. This study compared perceived health and gambling problems among 43 incarcerated older adults from two county jails in the midwestern United States. Results from the South Oaks Gambling Screen indicated 48.83% of the sample scored in the problem or pathological range. Short Form-36 results were compared with U.S. norms for ages 55 to 64 and showed significantly lower perceived health scores on Role-Physical, Bodily Pain, Mental Health, Social Functioning, and Role-Emotional subscales. The problem and pathological gamblers showed significantly lower social functioning than the recreational gamblers. Assessment of health conditions and gambling behaviors is important for quantifying current and anticipated burdens of these conditions on correctional health care systems and the community.