During the last decade, the healthcare topic has moved on the top of the development agenda not only for private organizations but also for public administrations. The information technology advances in the healthcare sector have designed an innovative model, the so-called eHealth, that leverages the Cloud Computing paradigm. Even more, with the medical devices (seen as IoT devices) proliferation, there have been introduced new challenges for the Cloud-IoT centric infrastructure. In this context, traditional Health Information Technology (HIT) systems present several limitations, such as scalability, faulttolerance, interoperability, data management and so on. Starting from the experience reported at ISASI-CNR (ME), a healthcare and research center, in this paper, we motivate the need to move the traditional HIT systems into innovative infrastructures based on the Osmotic Computing paradigm. In particular, we introduce two real uses cases, Ataxia and Dyslexia projects.