This study evaluates the utility of a stress and coping paradigm for explanining individual differences in psychological adjustment to chronic illness. Using data from the first wave of a longitudinal study of 170 middle-aged and elderly adults faced with one of four chronic illnesses (hypertension, diabetes mellitus, cancer and rheumatoid arthritis), this paper examines the relationship between the stresses of chronic illness and coping, and the ability of coping to explain psychological adjustment. Results show coping strategy use tends to be minimally explained by medical diagnosis. Cognitive strategies, including information seeking, are related to positive affect while emotional strategies, particularly those involving avoidance, blame and emotional ventilation, are related to negative affect, lowered self-esteem and poorer adjustment to illness. While the findings suggest that a stress and coping model may be valuable in understanding adjustment among the chronically ill, the general modesty of coping effects and the failure of the stress buffering hypothesis to explain adjustment indicates a need for new research approaches and some modification of current theories of coping.