Automating Empathy assesses technologies used to gauge how people are feeling. The book begins by historically situating the belief that by reading the body and its expressions one might ‘feel-into’ another. Finding this premise to be epistemologically problematic, the book then progresses to highlight the role of ethics. Automating Empathy advances a ‘hybrid’ approach to questions of technology and ethics, which starts from the position that people are entangled in new technologies. The book is pluralistic, attending to philosophies well-equipped to deal with questions of what is collectively good for society in relation to technologies that interact with intimate dimensions of human life. With early chapters introducing recurrent arguments and positions, the second part of the book addresses technologies and organisational uses. These include education and uses of automated empathy in classrooms and online settings; cars and transport, where cameras and other sensors gauge states such as fatigue, anger, and other emotions, and where cars themselves are design to feel; usage in the workplace, including assessment of bodies and voices in physical sites of work and online settings, and gauging of emotion through proxies in gig work settings; development of brain–computer interfaces that have scope to impact on multiple aspects of everyday life; and finally, renewed interest in enabling people to sell data about themselves. The book concludes automated empathy and its deployment needs to be inverted if systems are to function ethically.