We examined the prevalence of self-reported chronic conditions and out-of-pocket spending using the 2005 Medical Expenditure Panel Survey (MEPS) and made comparisons to previously published MEPS data. Our study found that the prevalence of self-reported chronic conditions is increasing among not only the old-old but also people in midlife and earlier old age. The greatest growth occurred in the number of people affected by multiple chronic diseases, a group with sizable out-of-pocket spending. Policymakers should be aware that cost sharing at the point of care can disproportionately burden people with chronic conditions and discourage adherence to drugs that prevent disease progression.