Abstract This article is a retrospective overview of work performed in the domain of Active Assisted Living over a span of almost 18 years. The authors have been creating and refining artificial intelligence (AI) and robotics solutions to support older adults in maintaining their independence and improving their quality of life. The goal of this article is to identify strong features and general lessons learned from those experiences and conceive guidelines and new research directions for future deployment, also relying on an analysis of similar research efforts. The work considers key points that have contributed to increase the success of the innovative solutions grounding them on known technology acceptance models. The analysis is presented with a threefold perspective: A Technological vision illustrates the characteristics of the support systems to operate in a real environment with continuity, robustness, and safety; a Socio-Health perspective highlights the role of experts in the socio-assistance domain to provide contextualized and personalized help based on actual people’s needs; finally, a Human dimension takes into account the personal aspects that influence the interaction with technology in the long term experience. The article promotes the crucial role of AI and robotics in ensuring intelligent and situated assistive behaviours. Finally, considering that the produced solutions are socio-technical systems, the article suggests a transdisciplinary approach in which different relevant disciplines merge together to have a complete, coordinated, and more informed vision of the problem.