ABSTRACT Purpose To evaluate factors associated with a higher completion rate of annual diabetic eye examinations. Methods This retrospective, cross-sectional study included patients diagnosed with diabetes mellitus (DM) who were aged 18–75 years and receiving primary care in a suburban integrated delivery network (IDN). Patient demographic, sociomedical, biometric characteristics, and Healthcare Effectiveness Data and Information Set (HEDIS) measures within the Comprehensive Diabetes Care bundle were extracted from the electronic health record (EHR) and analyzed by using multivariate logistic regression to assess factors associated with completion of an eye exam (retinal) performed during the study year. Results Among 19,901 primary care patients with DM, 35.15% completed an eye examination in 2021. After adjusting for demographic and biometric characteristics, the two factors most closely associated with completing a diabetic eye examination were having had a primary care office visit (adjusted odds ratio [aOR], 3.525; 95% confidence interval [CI], 3.210–3.871, p < 0.001) or an eye examination in the prior year (aOR, 2.948; 95% CI, 2.752–3.158, p < 0.001). The next most important factor to emerge was having an activated, online patient portal (PP; aOR, 1.737; 95% CI, 1.592–1.896; p < 0.001) or PP recently activated within the prior year (aOR, 1.387; 95% CI, 1.220–1.576, p < 0.001). Conclusions Surveillance for diabetic retinopathy relies on annual diabetic eye examinations yet adherence to that standard remains unacceptably low. Our study suggests that engagement of patients through an online PP could help increase this rate.