ICTs offer great opportunities for delivering telemedicine and social care in a number of domains including services for the elderly. This area of application, however, presents many challenges at many different levels. The purpose of this chapter is to describe an approach followed, and explore some lessons learned in Bologna (Italy). The stated objective of these developments was to maintain independent living, in their own homes, by elderly people for as long as possible and as cost effectively as possible. Thus the approach was an attempt to address the challenges both of the quality and the economics of care. Part of the background to the project was that, over the previous 10 years, more than three hundred elderly people had been involved in different home care projects in the Municipality. These initiatives started with traditional approaches to the integration of home care applications (telemedicine devices or software applications) using proprietary and ad hoc mechanisms and culminated in the development of the concept of a technical and organizational platform with the potential to overcome many of the problems of traditional e-Care applications and to exploit some of the new potentialities offered by network technologies such as eHealth and web 2.0 in health.