In the last years, there has been a growing interest in health mobile applications. Great benefits could be gained by seemingly “simple” solutions if these were designed to build a bridge between doctors and patients. In this paper, we describe a mobile health solution for patients allowing them to measure and record accurately their blood pressure at home, helping doctors to diagnose hypertension. An accurate measurement of the blood pressure, in fact, is a prerequisite for appropriate management of hypertension, a condition causing many serious diseases. The peculiarity of the hypertension kit is that the system requires interaction between the patients and their general practitioner. Finally, we present a pilot study carried out to evaluate the acceptability of the technologies, the compliance of patient to the self-monitoring procedure and the perceived benefits and disadvantages of both doctor and patients in using this kit.