Assistive technologies, such as telecare monitoring applications installed in the home, are being promoted to help reduce pressure on health care systems caused by an aging population and as such promise a large market for new products. However, despite many projects undertaken by commercial companies, and despite significant investments both by the companies and by national and international funding programs in the EU, such systems are not widespread. This paper reports on a retrospective study of the development of one early system, HandyHelper. We were interested in what challenges the development team faced and why the system is no longer on the market. Qualitative research methods were applied, including document analysis and interviews of key people involved in its development. Even though the system worked technically, the input of older users was sought, and a pilot installation was run, the development was stopped. The findings from a thematic analysis point to complex issues. Some problems were avoidable, e.g., by providing more support for new users, though other problems point to inherent tensions, such as the different needs of sensor-based security features and interactive services aimed at the older users. Yet other aspects are outside of the developer’s control, such as available public funding. We summarize these findings and suggest lessons learnt for future projects.