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.
Despite the fact that ALICE relies on such an old codebase, the bot offers users a remarkably accurate conversational experience. Of course, no bot is perfect, especially one that’s old enough to legally drink in the U.S. if only it had a physical form. ALICE, like many contemporary bots, struggles with the nuances of some questions and returns a mixture of inadvertently postmodern answers and statements that suggest ALICE has greater self-awareness for which we might give the agent credit.
Tay, an AI chatbot that learns from previous interaction, caused major controversy due to it being targeted by internet trolls on Twitter. The bot was exploited, and after 16 hours began to send extremely offensive Tweets to users. This suggests that although the bot learnt effectively from experience, adequate protection was not put in place to prevent misuse.[56]
However, the revelations didn’t stop there. The researchers also learned that the bots had become remarkably sophisticated negotiators in a short period of time, with one bot even attempting to mislead a researcher by demonstrating interest in a particular item so it could gain crucial negotiating leverage at a later stage by willingly “sacrificing” the item in which it had feigned interest, indicating a remarkable level of premeditation and strategic “thinking.”

ELIZA's key method of operation (copied by chatbot designers ever since) involves the recognition of clue words or phrases in the input, and the output of corresponding pre-prepared or pre-programmed responses that can move the conversation forward in an apparently meaningful way (e.g. by responding to any input that contains the word 'MOTHER' with 'TELL ME MORE ABOUT YOUR FAMILY').[9] Thus an illusion of understanding is generated, even though the processing involved has been merely superficial. ELIZA showed that such an illusion is surprisingly easy to generate, because human judges are so ready to give the benefit of the doubt when conversational responses are capable of being interpreted as "intelligent".
Previous generations of chatbots were present on company websites, e.g. Ask Jenn from Alaska Airlines which debuted in 2008[27] or Expedia's virtual customer service agent which launched in 2011.[27][28] The newer generation of chatbots includes IBM Watson-powered "Rocky", introduced in February 2017 by the New York City-based e-commerce company Rare Carat to provide information to prospective diamond buyers.[29][30]

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: