The aim of this study was to determine the association between health insurance/health benefit and medication adherence amongst adult diabetic patients in Kingston, Jamaica. In this cross-sectional study, the target population was diabetics who attended the diabetic outpatient clinics in health centres in Kingston. Two health centres were selectively chosen in Kingston. All diabetic patients attending the diabetic clinics and over the age of 18 were conveniently sampled. An interviewer-administered questionnaire was utilized. Health insurance/health benefit was assessed by this questionnaire. Adherence was measured by patients’ self reports of medication usage in the previous week. The Chi-squared was used to determine significance of associations. The sample population was 76% female and 24% male. Type 2 diabetics comprised 93.8%. More than 95% of patients were over the age of 40. Approximately 32% of participants were employed. Approximately 75% of patients had health insurance/health benefit. Among those who had health insurance or health benefit, 71.5% was adherent and 28.5% was non-adherent. This difference was statistically significant (χ2=6.553, p = 0.01). Prevalence of medication non-adherence was 33%.In Kingston, diabetic patients who are adherent are more likely to have health insurance/health benefit (p = 0.01).