The interconnection of Internet of Things (IoT) devices has heralded automation and control solutions in almost all technology and non-technical fields. In healthcare, IoT devices are used to monitor and assess patient response to treatment in different environmental contexts on a global scale. In agriculture, the IoT is being used to develop smart early warning systems to monitor factors that adversely influence food production and crop yields such as diseases, adverse weather, politicoeconomic trends, natural disasters, and internal supply chains. In manufacturing, IoT sensor networks are used to collect critical production data, which are turned into valuable insights about the efficiency and resilience of the manufacturing operations. In smart cities, the IoT promises a future where driverless transport systems dynamically reorganise and re-route in anticipation to changing traffic demands and conditions. In smart living, IoT systems are learning from our behaviour and adapting our environments in real-time to our changing needs and circumstances. Almost all IoT implementations are now underpinned by some element of AI in the data analysis. AI enables IoT systems to extend their capability beyond things networks that are limited to the analysis of raw data, to systems that offer insights and predictability using the generated data—from assisted intelligence that analyses streams of data and to predict possible outcomes, to augmented intelligence that generates basic responses based on the analysis of data streams, to autonomous intelligence that is able to anticipate change and adapt its environment autonomously. This Special Issue will collect original research papers and novel insights into the modelling, design, implementation, testing and experience of using of AI-enabled IoT systems.