The progression of hypertensive involvement toward heart failure includes myocardial fibrosis and changes of left ventricular (LV) geometry. In the presence of these abnormalities, diastolic abnormalities occur and are defined as LV diastolic dysfunction (DD). They include alterations of both relaxation and filling, precede alterations of chamber systolic function and can induce symptoms of heart failure even when ejection fraction is normal. The prevalence of heart failure with normal ejection fraction (HFNEF) increased over time whereas the rate of death from this disorder remained unchanged. In this view, diagnosis, prognosis, and therapeutic management of DD and HFNEF in hypertensive patients is a growing public health problem. DD may be asymptomatic and identified occasionally during a Doppler-echocardiographic examination. This tool has gained, therefore, important clinical position for diagnosis of DD. Comprehensive assessment of diastolic function should be done not by a simple classification of DD progression but by estimating the degree of LV filling pressure (FP), a true determinant of symptoms and prognosis. This can be obtained by different ultrasound maneuvers/tools but the ratio between transmitral E velocity and pulsed tissue Doppler-derived early diastolic velocity (E/e' ratio) is the most feasible and accurate. The identification of left atrial enlargement may be useful in uncertain cases. The recommended management of DD in hypertensive patients should correspond to blood pressure (BP) lowering and to the attempt of reducing LV mass and normalizing LV geometry. Prospective studies with well-defined entry criteria are needed to establish whether this approach could reflect a better prognosis.