Cigarette smoking is the leading cause of preventable disease and is the cause of nearly 1 in 5 deaths in the United States. The prevalence of smoking has had a leveling off effect after many years of significant decline. Certain subgroups of the population, such as those with low income and certain illnesses, continue to smoke at disproportionately high rates. Reasons for these disparities in smoking rates are complex. Developing a better understanding of the issues related to persistent smoking particularly for those with medical illness and limited access to cessation resources can help focus interventions to help these high risk smokers quit. This dissertation includes a systematic review of the literature associated with hardcore smoking; an analysis of the reliability and validity of a self-efficacy instrument in a sample of low-SES, medically ill smokers; and the results of a cross-sectional, non-experimental study exploring the relationship between smoking-related factors and planning to quit in a sample of medically ill smokers. A sample of 70 current and recent smokers was surveyed at a free clinic. Quitting self-efficacy was measured using an instrument not previously tested in a rural, medically ill sample. Modifications to the survey were made based on qualitative interviews with smokers and a single question measuring self-efficacy was also tested. There was a high correlation among the self-efficacy measures (Spearman’s rho .99, p < .001) and between the longer instrument and the single question (Spearman’s rho .65, p < .001). Each measure demonstrated acceptable reliability and validity. In the study exploring potential factors associated with planning to quit, the number of prior quit attempts and confidence to quit explained 43% of the variance in those planning versus not planning to quit. Providing interventions focused on increasing confidence and experience with quit attempts can be effective in promoting a plan to quit in this group of smokers who, because of their medical illness, can benefit significantly from cessation. Research is needed to explore cessation outcomes when employing these targeted interventions with medically ill smokers in rural areas.