The authors analyze correlates of the direction and magnitude of changes in out-of-pocket (OOP) payments for dental care by older Americans over a recent 4-year period. They analyzed data from the 2006 and 2008 waves of the Health and Retirement Study. They estimated multinomial logistic models of the direction and linear regression models of the amounts of OOP changes over survey periods. Financial-based factors were more strongly associated with the direction and magnitude of changing self-payments for dental care than were health factors. Findings suggested that dental coverage, income, and wealth and changes in these financial factors were more strongly correlated with the persistence of and changes in OOP payments for dental care over time than were health status and changes in health status. The sensitivity to dental coverage changes should be considered as insurance and retirement policy reforms are deliberated.