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.