Possible design guidelines are suggested, reflecting different chatbot user motivations.The Turing Test was invented and developed by the eponymous British mathematician, computer scientist and logician Alan Turing in 1950. The findings can help developers facilitate better hu-man–chatbot interaction experiences in the future. The findings are discussed in terms of the uses and gratifications theory, and they provide insight into why people choose to interact with automated agents online. Chatbot users also reported motivations pertaining to entertainment, social and relational factors, and curiosity about what they view as a novel phenomenon. The most frequently reported moti-vational factor is ' productivity ' chatbots help users to obtain timely and efficient assistance or information. The study identifies key motivational factors driving chatbot use. In this study, an online questionnaire asked chatbot users (N = 146, aged 16–55 years) from the US to report their reasons for using chatbots. However, no studies have empirically investigated people's motivations for using chatbots. There is a growing interest in chatbots, which are machine agents serving as natural language user interfaces for data and service providers. This may be a failure on the part of the academic AI community for ignoring the Turing test as an engineering challenge. The authors find that synthetic textual systems, none of which are backed by academic or industry funding, are, on the whole and more than half a century since Weizenbaum’s natural language understanding experiment, little further than Eliza in terms of expressing emotion in dialogue. This paper provides an insight into emotion content in the entries since the 2005 Chatterbox Challenge. Loosely based on Turing’s viva voca interrogator-hidden witness imitation game, a thought experiment to ascertain a machine’s capacity to respond satisfactorily to unrestricted questions, the contest provides a platform for technology comparison and evaluation. The 2010 instantiation was the tenth consecutive contest held between March and June in the 60th year following the publication of Alan Turing’s influential disquisition ‘computing machinery and intelligence’. Chatterbox Challenge is an annual web-based contest for artificial conversational systems, ACE.

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