Evidence that hypertension is the most importat global risk factor for cardiovascular morbidity and mortality, and demonstration of the cardiovascular protection offered by antihypertensive treatment, have been based on upper-arm cuff blood pressure (BP) measurements. This approach is recommended by current hypertension guidelines for BP measurement in clinical practice, as well as for validation of novel BP measuring devices. However, the spot or intermittent BP measurements in static conditions allowed by arm-cuff devices are unable to identify and track the continuous and rapid BP changes characterizing daily life. Moreover, cuff-based BP measurements are exposed to errors related to cuff size, shape and positioning, and cuff inflation may itself induce an alerting response and produce discomfort in the users during daily activities and in particular during sleep, which may modify the measured BP levels. To face these issues, use of continuous recordings techniques, not based on arm-cuff inflation, would be required. This is possible through intra-arterial recordings, which however are not feasible in daily practice because of their invasiveness. An alternative solution is represented by photoplethysmographic volume-clamp method for finger BP monitoring which, however, is difficult to implement in clinical practice because of its cost and complexity. Technological progress is now offering an increasingly large and heterogeneous series of cuffless BP monitors, which estimate BP based on sensors, signal processing and algorithms embedded in wearable devices, smartphones or pocket devices. These cuffless devices might allow for comfortable and continuous BP recordings, detecting rapid BP changes during day and night sleep, thus offering information on both short, mid and long term BP variability. Cuffless devices might also be useful for continuous non invasive BP monitoring in different clinical settings, including ICUs, during anaesthesia, in patients with arrhythmias, hypotension/syncope, and other transient conditions affecting BP levels and variability. Moreover, cuffless BP measurement devices connected to telemonitoring facilities or smartphones apps may improve patients empowerment, adherence to treatment and long-term BP control. In spite of all these potential advantages, however, cuffless BP devices have to face specific accuracy issues, which would need refinement of specific validation protocols aimed at testing the need of individual calibration, the stability of measurements after calibration and the device actual ability to track BP changes before they might be recommended for clinical use.