The main goal of this research is to provide a comprehensive understanding of the actual progresses in artificial intelligence, with emphasis on chatbots as emerging forms of customer assistance in online retailing. Drawing upon an analysis of the chatbot patents in the past 20 years, our findings show the increasing technology push towards the adoption of new conversational agents based on natural language. Findings also highlight the extent to which the research and development efforts are attempting to improve artificial intelligence systems that characterize chatbots. To this end, technology advancements are mainly focusing on: (i) improving chatbot ability to automatically draw inferences on users starting from multiple data sources, and (ii) using consumers’ knowledge adaptively to provide more customized solutions. Finally, results show the tight relationship between the digital assistants’ analytical skills and their ability to automatically interact with the users.