In 2000, almost one in six State prisoners and one in four Federal inmates reported having a physical ailment. The medical problems, many of which existed before incarceration, were heart and circulatory (10.4 percent), respiratory (4.4 percent), and liver problems (1.4 percent). Rates of infectious diseases like HIV/AIDS, sexually transmitted diseases, Hepatitis B and C, and tuberculosis were much higher among those incarcerated than those in the general community. These health problems are compounded because many inmates have limited access to health care before and after their incarceration. This research examines the relationships between an extensive criminal history and drug use, physical and mental health problems, and treatment services. Participants consisted of 661 males from 4 Kentucky State Correctional facilities. Characteristics of the participants included being a chronic drug abuser, not having past violent charges of rape or murder, being scheduled for parole consideration within the next 3 months, and having at least 3 months on the street prior to incarceration. They completed a four-page questionnaire and were interviewed. Results show that, after controlling for age, incarcerated chronic drug abusers with more extensive criminal histories had longer addiction careers with alcohol, marijuana, cocaine, amphetamines, sedatives, and multiple drugs. A more extensive criminal history was associated with higher rates of reproductive/urinary, musculoskeletal, liver, circulatory, and gastrointestinal problems. There were more overall physical problems than individuals with a less extensive criminal history. Those with extensive criminal histories reported more emergency room use, more hospitalizations, and more drug and alcohol treatment admissions. Little support for the relationship between mental health and crime was found in this sample. More attention should be paid to specific offender populations for health care in correctional settings. 2 figures, 2 tables, 40 references