This is where most applications of NLP struggle, and not just chatbots. Any system or application that relies upon a machine’s ability to parse human speech is likely to struggle with the complexities inherent in elements of speech such as metaphors and similes. Despite these considerable limitations, chatbots are becoming increasingly sophisticated, responsive, and more “natural.”

Disney invited fans of the movie to solve crimes with Lieutenant Judy Hopps, the tenacious, long-eared protagonist of the movie. Children could help Lt. Hopps investigate mysteries like those in the movie by interacting with the bot, which explored avenues of inquiry based on user input. Users can make suggestions for Lt. Hopps’ investigations, to which the chatbot would respond.
Chatbots are predicted to be progressively present in businesses and will automate tasks that do not require skill-based talents. Companies are getting smarter with touchpoints and customer service now comes in the form of instant messenger, as well as phone calls. IBM recently predicted that 85% of customer service enquiries will be handled by AI as early as 2020.[62] The call centre workers may be particularly at risk from AI.[63]
Sometimes it is hard to discover if a conversational partner on the other end is a real person or a chatbot. In fact, it is getting harder as technology progresses. A well-known way to measure the chatbot intelligence in a more or less objective manner is the so-called Turing Test. This test determines how well a chatbot is capable of appearing like a real person by giving responses indistinguishable from a human’s response.
Interface designers have come to appreciate that humans' readiness to interpret computer output as genuinely conversational—even when it is actually based on rather simple pattern-matching—can be exploited for useful purposes. Most people prefer to engage with programs that are human-like, and this gives chatbot-style techniques a potentially useful role in interactive systems that need to elicit information from users, as long as that information is relatively straightforward and falls into predictable categories. Thus, for example, online help systems can usefully employ chatbot techniques to identify the area of help that users require, potentially providing a "friendlier" interface than a more formal search or menu system. This sort of usage holds the prospect of moving chatbot technology from Weizenbaum's "shelf ... reserved for curios" to that marked "genuinely useful computational methods".

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In 1950, Alan Turing's famous article "Computing Machinery and Intelligence" was published,[7] which proposed what is now called the Turing test as a criterion of intelligence. This criterion depends on the ability of a computer program to impersonate a human in a real-time written conversation with a human judge, sufficiently well that the judge is unable to distinguish reliably—on the basis of the conversational content alone—between the program and a real human. The notoriety of Turing's proposed test stimulated great interest in Joseph Weizenbaum's program ELIZA, published in 1966, which seemed to be able to fool users into believing that they were conversing with a real human. However Weizenbaum himself did not claim that ELIZA was genuinely intelligent, and the introduction to his paper presented it more as a debunking exercise: