Recent studies support the concept that the retinal vasculature may provide a summary measure of lifetime exposure to the effects of hyperglycemia. Advances in retinal photographic techniques and in image analysis have allowed objective and precise in vivo measurement of retinal vascular changes. In particular, quantitative assessment of retinopathy signs and measurement of retinal vascular caliber have greatly increased our knowledge of early microcirculatory alterations in prediabetes, diabetes, and diabetic micro- and macrovascular complications. Data from recent population-based studies suggest that retinal arteriolar and venular caliber changes reflect different pathophysiologic processes. Retinal arteriolar narrowing, for example, is associated with risk of diabetes and coronary artery disease, whereas retinal venular widening is associated with development and progression of diabetic retinopathy and risk of stroke. Studying these changes offers the potential to improve our understanding of the early pathophysiologic pathways of diabetes development and its complications. Future research will assess the ability of retinal vascular imaging to provide clinically useful prognostic information for patients with diabetes.