Understanding the relationships among diabetes, teeth present, and dental insurance is essential to improving primary and oral health care. Participants were older adults who attended senior centers in northern Manhattan (New York, N.Y.). Sociodemographic, health, and health care information were obtained via intake interviews, number of teeth present via clinical dental examinations, and glycemic status via measurement of glycosylated hemoglobin (HbA1c). Complete data on dental insurance coverage status for 785 participants were available for analysis (1,015 after multiple imputation). For participants with no dental insurance and any private/other dental insurance, number of teeth present is less for participants with diabetes than for participants without diabetes; however, for participants with Medicaid coverage only, the relationship is reversed. Potential explanations include the limited range of dental services covered under the Medicaid program, inadequate diabetes screening and monitoring of Medicaid recipients, and the poor oral and general health of Medicaid recipients.