Diabetic retinopathy screening traditionally relies on fundus photography, requiring specialized equipment and expertise often unavailable in primary care and resource limited settings. We developed and validated a deep learning (DL) system for automated diabetic classification using anterior segment ocular imaging a readily accessible alternative utilizing standard photography equipment. The system leverages visible biomarkers in the iris, sclera, and conjunctiva that correlate with systemic diabetic status. We systematically evaluated five contemporary architectures (EfficientNet-V2-S with self-supervised learning (SSL), Vision Transformer, Swin Transformer, ConvNeXt-Base, and ResNet-50) on 2,640 clinically annotated anterior segment images spanning Normal, Controlled Diabetic, and Uncontrolled Diabetic categories. A tailored preprocessing pipeline combining specular reflection mitigation and contrast limited adaptive histogram equalization (CLAHE) was implemented to enhance subtle vascular and textural patterns critical for classification. SSL using SimCLR on domain specific ocular images substantially improved model performance.EfficientNet-V2-S with SSL achieved optimal performance with an F1-score of 98.21%, precision of 97.90%, and recall of 98.55% a substantial improvement over ImageNet only initialization (94.63% F1). Notably, the model attained near perfect precision (100%) for Normal classification, critical for minimizing unnecessary clinical referrals.