Our research explores the possibility to assist employees close or beyond retiring age in the workplace and enhance their, and general, safety by monitoring the personal stress state via wearable and environmental Internet of Things (IoT) sensors and by suggesting proper actions to reduce stress levels and enhance well-being at work. This paper presents the goals and the technological issues, investigated in “AmbienT Response to Avoid Negative Stress and enhance SAFEty” (Trans.Safe) EU AAL JP project, along with the general architecture, the preliminary implementations and some anthropological issues, describing the current state of the research and development.