Older offenders (offenders 50 years and older) are a distinct groups within the U.S. correctional system. Studies 1 and 2 were intended to investigate mental health and stressors among jailed older offenders. Study 1 examined the prevalence rates of mental health disorders and explored the relationship between mental health disorders and stressors. Participants 50 years and older (N=330) from the 2002 wave of the Survey of Inmates in Local Jails (SILJ) were studied via descriptive analysis, factor analysis, and a logistic regression to determine which variables were related to the probability of having a mental health problem. 65.8% of participants had at least one mental health disorder, with high rates of substance abuse reported. Individuals who were between 50-59 years of age (compared with those over 60) and individuals who were unmarried had a significantly increased likelihood of being in the group with mental health problems. Caucasians and participants with fewer instances of childhood abuse were significantly less likely to be in the group with mental health problems. Study 2 compared stressors over the life course between late life first time offenders (offenders whose first arrest occurred at age 50 or older; hereafter LLFTO) and habitual older offenders, who had one or more arrests. This study descriptively and comparatively analyzed individuals who were age 50 or older at arrest and reported their age of first arrest from the 1996 and 2002 waves of SILJ, with a final sample of 62 LLFTOs and 357 older offenders with previous arrests. LLFTOs were significantly older, more likely to be married, and more likely to be female. Over the life course, LLFTOs were more likely to have lived with their father or other relative as children, were less likely to have used alcohol or had friends with a history of delinquency as adolescents, and were less likely to have been homeless as adults. This dissertation research shows that older offenders have a variety of needs during their incarceration that may persist upon release. Addressing mental health disorders, and stressors across the life span, is needed to promote successful aging.