This book constitutes selected papers presented at the First International Workshop on Deceptive AI, DeceptECAI 2020, held in conjunction with the 24th European Conference on Artificial Intelligence, ECAI 2020, in Santiago de Compostela, Spain, in August 2020, and Second International Workshop on Deceptive AI, DeceptAI 2021, held in conjunction with the 30th International Joint Conference on Artificial Intelligence, IJCAI 2021, in Montreal, Canada, in August 2021. Due to the COVID-19 pandemic both conferences were held in a virtual mode. The 12 papers presented were thoroughly reviewed and selected from the 16 submissions. They present recent developments in the growing area of research in the interface between deception and AI.