These two volumes constitute the proceedings of the 21st International Conference, ICSOC 2023, held Rome, Italy, during November 28–December 1, 2023. The 35 full papers and the 10 short papers included in this volume were carefully reviewed and selected from 208 submissions. The volumes focus on cutting-edge topics like artificial intelligence, machine learning, big data analytics, the Internet of Things (IoT), and emerging technologies such as quantum computing, blockchain, chatbots, and sustainable green IT solutions.