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.”

Jabberwacky learns new responses and context based on real-time user interactions, rather than being driven from a static database. Some more recent chatbots also combine real-time learning with evolutionary algorithms that optimise their ability to communicate based on each conversation held. Still, there is currently no general purpose conversational artificial intelligence, and some software developers focus on the practical aspect, information retrieval.


^ "From Russia With Love" (PDF). Retrieved 2007-12-09. Psychologist and Scientific American: Mind contributing editor Robert Epstein reports how he was initially fooled by a chatterbot posing as an attractive girl in a personal ad he answered on a dating website. In the ad, the girl portrayed herself as being in Southern California and then soon revealed, in poor English, that she was actually in Russia. He became suspicious after a couple of months of email exchanges, sent her an email test of gibberish, and she still replied in general terms. The dating website is not named. Scientific American: Mind, October–November 2007, page 16–17, "From Russia With Love: How I got fooled (and somewhat humiliated) by a computer". Also available online.

However, as irresistible as this story was to news outlets, Facebook’s engineers didn’t pull the plug on the experiment out of fear the bots were somehow secretly colluding to usurp their meatbag overlords and usher in a new age of machine dominance. They ended the experiment due to the fact that, once the bots had deviated far enough from acceptable English language parameters, the data gleaned by the conversational aspects of the test was of limited value.

Enter Roof Ai, a chatbot that helps real-estate marketers to automate interacting with potential leads and lead assignment via social media. The bot identifies potential leads via Facebook, then responds almost instantaneously in a friendly, helpful, and conversational tone that closely resembles that of a real person. Based on user input, Roof Ai prompts potential leads to provide a little more information, before automatically assigning the lead to a sales agent.
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]
This chatbot aims to make medical diagnoses faster, easier, and more transparent for both patients and physicians – think of it like an intelligent version of WebMD that you can talk to. MedWhat is powered by a sophisticated machine learning system that offers increasingly accurate responses to user questions based on behaviors that it “learns” by interacting with human beings.
AI-driven automation in each of these areas can streamline how enterprises train, manage, and work with seasonal, temporary, part-time, and full-time employees. However, it is important to consider the challenges surrounding information security, legal boundaries, extensibility, and audit logging when making the decision to get started using bots for HR.
The most advanced bots are powered by artificial intelligence, helping it to understand complex requests, personalize responses, and improve interactions over time. This technology is still in its infancy, so most bots follow a set of rules programmed by a human via a bot-building platform. It's as simple as ordering a list of if-then statements and writing canned responses, often without needing to know a line of code.
According to the Journal of Medical Internet Research, "Chatbots are [...] increasingly used in particular for mental health applications, prevention and behavior change applications (such as smoking cessation or physical activity interventions).".[48] They have been shown to serve as a cost-effective and accessible therapeutic agents for indications such as depression and anxiety.[49] A conversational agent called Woebot has been shown to significantly reduce depression in young adults.[50]
Efforts by servers hosting websites to counteract bots vary. Servers may choose to outline rules on the behaviour of internet bots by implementing a robots.txt file: this file is simply text stating the rules governing a bot's behaviour on that server. Any bot that does not follow these rules when interacting with (or 'spidering') any server should, in theory, be denied access to, or removed from, the affected website. If the only rule implementation by a server is a posted text file with no associated program/software/app, then adhering to those rules is entirely voluntary – in reality there is no way to enforce those rules, or even to ensure that a bot's creator or implementer acknowledges, or even reads, the robots.txt file contents. Some bots are "good" – e.g. search engine spiders – while others can be used to launch malicious and harsh attacks, most notably, in political campaigns.[2]
According to the Journal of Medical Internet Research, "Chatbots are [...] increasingly used in particular for mental health applications, prevention and behavior change applications (such as smoking cessation or physical activity interventions).".[48] They have been shown to serve as a cost-effective and accessible therapeutic agents for indications such as depression and anxiety.[49] A conversational agent called Woebot has been shown to significantly reduce depression in young adults.[50]
In one particularly striking example of how this rather limited bot has made a major impact, U-Report sent a poll to users in Liberia about whether teachers were coercing students into sex in exchange for better grades. Approximately 86% of the 13,000 Liberian children U-Report polled responded that their teachers were engaged in this despicable practice, which resulted in a collaborative project between UNICEF and Liberia’s Minister of Education to put an end to it.
There are several defined conversational branches that the bots can take depending on what the user enters, but the primary goal of the app is to sell comic books and movie tickets. As a result, the conversations users can have with Star-Lord might feel a little forced. One aspect of the experience the app gets right, however, is the fact that the conversations users can have with the bot are interspersed with gorgeous, full-color artwork from Marvel’s comics. 
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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