Approximately half of U.S. adults have been diagnosed with at least one type of chronic illness (e.g., diabetes, heart disease, multiple sclerosis). With a diagnosis of chronic illness comes a mark of stigma, or social devaluation and discrediting due to the chronic illness. People living with chronic illnesses may come to anticipate stigma by expecting to be treated with prejudice, discrimination, and stereotyping in the future because of their chronic illness. The current dissertation explores how anticipated stigma undermines the quality of life of people living with chronic illnesses and examines a strategy to disrupt this negative relationship. Study 1 evaluated the psychometric properties of the Chronic Illness Anticipated Stigma Scale, which measures anticipated stigma from friends and family members, employers, and healthcare workers. Results demonstrate that the CIASS is both reliable and valid. Study 2 used the CIASS to explore the relationship between anticipated stigma and quality of life in a cross-sectional survey of community members living with chronic illnesses. Results provide evidence that anticipated stigma from friends and family members, employers, and healthcare workers is associated with decreased quality of life. Results further suggest that increased stress and decreased social support act as partial mediators of the relationship between anticipated stigma and quality of life. Study 3 examined a strategy designed to disrupt the relationship between anticipated stigma and quality of life by alleviating stress associated with anticipated stigma. This strategy involved attempting to increase perceptions of resources with which to handle discrimination. Although the experimental manipulation failed to impact perceptions of resources or stress, additional analyses suggest that trait-level perceived resources to handle discrimination may contribute to decreased stress in certain contexts. Research that continues to explore chronic illness stigma and examine ways to alleviate its impact on people living with chronic illnesses is critical to improving the health of a substantial number of U.S. adults.