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One major element of novelty of the 2007 European guidelines on hypertension refers to the concept of risk categorization, with the aim of obtaining a more precise definition of the hypertensive patient. This has lead to identification of different categories of cardiovascular risk, from the low to the very high. Studies performed in the past few years have shown that the very high risk category is quite common and it is not unusually accompanied by poor blood pressure control. Results of the ONgoing Telmisartan Alone and in combination with Ramipril Global Endpoint Trial (ONTARGET) and the Telmisartan Randomized AssessmeNt Study in ACEI iNtolerant subjects with cardiovascular Disease (TRANSCEND) have allowed us to better define the therapeutic approach to high-risk patients showing the favorable effects of either ramipril or telmisartan on blood pressure control and risk profile. Additionally, these studies have shown that discontinuation of antihypertensive treatment is not a rare phenomenon, which can be at least in part minimized by the use of drugs with a high tolerability profile, such as angiotensin II receptor blockers (ARBs), and more specifically telmisartan. This review article examines in depth the results of the two above-mentioned trials as well as their impact on guidelines on antihypertensive treatment.