Nowadays employment of new technologies has been established as an acceptable means to support daily living for different segment of young population, elderly or people with disabilities. In this context, new technological tools for telecare and Ambient Assisted Living can support people in their daily life activities. Several solutions have been demonstrated to support different level of services through seamless data acquisition or specific users interaction modalities. In such approach, services usability and accessibility are handled in design process itself and validated with small users' groups. Moreover, while service design and systems development have been extensively described in literature, the service deployment methodologies are not properly addressed and documented and proper reference guidelines are missing. The most common methodologies like Unified Process (UP) or ICONX can cover only the design and the development of telecare service without describing clearly the following phases of deployment and distribution: such phases have quite often very high risks witch have to be considered in advance. So, in this paper, we focus on the development of a methodology and structured approach to deploy telecare services. Based on the experience and outcome collected in the deployment of service in different European countries, this paper outline at methodological level the main criticism and issues encountered in telecare services deployment, tailoring and adapting the UP framework, in particular the "Transition phase", for such services.