We assessed whether retinal arteriolar narrowing and structural abnormalities independently predicted 5-year incident severe (grade 2 or 3) hypertension in an older population-based cohort. The Blue Mountains Eye Study baseline (1992 to 1994) examined 3654 residents aged 49 and older in 2 postal code areas, west of Sydney. Of the 2335 participants (75.1% of survivors) who returned at the 5-year examinations, 1319 were normotensive or had mild (grade 1) hypertension at baseline. Baseline retinal photographs were graded for focal retinal vessel wall signs and vessel diameters were measured. Participants were classified as having normal, high-normal blood pressure [BP] (systolic BP 121 to 139 mm Hg and/or diastolic BP 81 to 89 mm Hg), mild hypertension (systolic BP 140 to 159 mm Hg and/or diastolic BP 90 to 99 mm Hg), or severe hypertension if they had a previous diagnosis of hypertension and were receiving antihypertensive medications or had systolic BP > or =160 mm Hg and/or diastolic BP > or =100 mm Hg at examination. Incident severe hypertension was defined in persons who were free of severe hypertension at baseline but classified as having severe hypertension at the 5-year examinations. Of the 1319 baseline subjects at risk, 390 (29.6%) developed severe hypertension. After adjusting for age, sex, body mass index, smoking, glucose, and total cholesterol, generalized retinal arteriolar narrowing at baseline was associated with increased risk of incident severe hypertension (odds ratio 2.6; 95% confidence interval, 1.7 to 3.9) when comparing the narrowest versus widest quintile. This association remained significant after further adjustment for baseline mean arterial BP or BP status. Our findings support the hypothesis that small vessel structural changes may precede the development of severe hypertension.