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This book constitutes the proceedings of the 5th International Workshop on Chatbot Research and Design, CONVERSATIONS 2021, which was held during November 2021.Due to COVID-19 pandemic the conference was held online.The 12 papers included in this volume were carefully reviewed and selected from a total of 25 submissions. The papers in the proceedings are structured in four topical groups: Chatbot User Insight, Chatbots Supporting Collaboration and Social Interaction, and Chatbot UX and Design.

This book constitutes the proceedings of the 4th International Workshop on Chatbot Research and Design, CONVERSATIONS 2020, which was held during November 23-24, 2020, hosted by the University of Amsterdam. The conference was planned to take place in Amsterdam, The Netherlands, but changed to an online format due to the COVID-19 pandemic.The 14 papers included in this volume were carefully reviewed and selected from a total of 36 submissions. The papers in the proceedings are structured in four topical groups: Chatbot UX and user perceptions, social and relational chatbots, chatbot applications, and chatbots for customer service. The papers provide new knowledge through empirical, theoretical, or design contributions.