Although tremendous advances have been made in recent years, many real-world problems still cannot be solved by machines alone. Hence, the integration of Human Intelligence and Artificial Intelligence is needed. However, several challenges make this integration complex. The aim of this Special Issue was to provide a large and varied collection of high-level contributions presenting novel approaches and solutions to address the above issues. This Special Issue contains 14 papers (13 research papers and 1 review paper) that deal with various topics related to human-machine interactions and cooperation. Most of these works concern different aspects of recommender systems, which are among the most widespread decision support systems. The domains covered range from healthcare to movies and from biometrics to cultural heritage. However, there are also contributions on vocal assistants and smart interactive technologies. In summary, each paper included in this Special Issue represents a step towards a future with human-machine interactions and cooperation. We hope the readers enjoy reading these articles and may find inspiration for their research activities.