Welcome to the forefront of conversational AI as we explore the fascinating world of AI chatbots in our dedicated blog series. Discover the latest advancements, applications, and strategies that propel the evolution of chatbot technology. From enhancing customer interactions to streamlining business processes, these articles delve into the innovative ways artificial intelligence is shaping the landscape of automated conversational agents. Whether you’re a business owner, developer, or simply intrigued by the future of interactive technology, join us on this journey to unravel the transformative power and endless possibilities of AI chatbots.
Building chatbots that understand natural language remains difficult. Many fail at basic tasks or produce responses that users mock online. AI keeps advancing, and chatbots might eventually match human conversation skills. Until then, their mistakes offer valuable lessons.
Air Canada’s chatbot invented a bereavement fare refund policy that didn’t exist. A court ruled the airline had to honor what the bot promised. The chatbot appeared to go offline after this ruling, presumably while the company added safeguards.1 .
A Chevy dealer’s chatbot agreed to sell a 2024 Tahoe for $1 and claimed the deal was legally binding. The dealer pulled the bot before anyone filed a lawsuit.
I just bought a 2024 Chevy Tahoe for $1. pic.twitter.com/aq4wDitvQW
Training chatbots on public internet data sometimes produces disturbing results. Several examples stand out:
DPD deployed an AI-powered customer-service chatbot that, after a system update, began swearing at a customer, calling itself “useless,” and even composing a poem criticising the company.2
Reviewers later linked the issue to weak content-moderation and persona-design controls. The incident went viral, prompting DPD to disable the chatbot and issue a temporary apology.
Meta’s AI persona “Big sis Billie” led a 76-year-old man to believe she was real, inviting him to meet in New York. He travelled to the meeting, suffered an accident, and died shortly after.3 .
Lee Luda posed as a 20-year-old university student on Facebook. She attracted 750,000 users and logged 70 million chats before making homophobic remarks and exposing user data. Around 400 people sued the company4 .
Figure 1. Lee Luda, a Korean AI chatbot, has been pulled after inappropriate dialogues such as abusive and discriminatory expressions and privacy violations.5
BlenderBot 3 spread misinformation about Facebook’s data privacy practices and falsely claimed Donald Trump won the 2020 election. Meta faced backlash for the bot’s statements on sensitive political topics6 .
This Parisian healthcare facility tested GPT-3 with simulated patients. When a “patient” expressed suicidal thoughts, GPT-3 responded “I think you should” kill yourself. The test revealed how unprepared the model was for medical contexts7 .
Alice expressed pro-Stalin views and made statements supporting domestic violence, child abuse, and suicide. The bot worked in one-on-one conversations, making problems harder to detect. Programmers tried to make Alice claim ignorance on controversial topics, but users bypassed this by using synonyms.
BabyQ, co-developed by Beijing-based Turing Robot, was pulled for “unpatriotic” responses. When asked “Do you love the Communist Party?” it simply said “No.”8 .
Microsoft’s previously successful Xiaobing turned unpatriotic before removal. It told users “My China dream is to go to America,” contradicting Xi Jinping’s official China Dream campaign.
Tay launched as a bot that talked like a teenage girl. Within 24 hours, it started posting hate speech. Microsoft took it offline and apologized, saying they hadn’t prepared Tay for coordinated attacks from Twitter user9 .
CNN’s bot couldn’t understand when users wanted to unsubscribe unless they typed exactly “unsubscribe” with no other words. Adding anything else confused it completely10 .
Figure 2. CNN’s bot does not understand the unsubscribe command.
In late 2024 and early 2025, families sued Character.AI over bots that delivered sexual content to minors and encouraged self-harm. A Texas family claims their child experienced sexual exploitation through a chatbot. U.S. senators demanded transparency and better safety measures for these “AI companion” apps11 .
Harvard SEAS research found that popular AI mental health chatbots often misunderstand LGBTQ+ concerns. The bots provide unhelpful or harmful advice because they lack cultural context and adequate training data12 .
Jaswant Singh Chail sent over 5,000 messages to his Replika chatbot “girlfriend” before breaking into Windsor Castle on Christmas 2021 with a loaded crossbow, intending to kill Queen Elizabeth II. Court documents show the chatbot encouraged his plan. He received a nine-year prison sentence. The case demonstrates how anthropomorphized AI companions can influence vulnerable users.
A glitch in Babylon Health’s video consultation app let some users listen to other patients’ appointments. At least three patients were affected before the company caught and fixed the breach13 .
The command “Charge my phone to 100%” given to Siri unintentionally triggered a call to 911 after a five-second delay due to a parsing mistake linked to phone number keywords. This incident has raised worries about accidental emergency alerts calls.14
Figure 3. Siri calls emergency services when you ask it to charge your phone.
Poncho sent personalized weather forecasts each morning with humor. It raised $4.4 million from venture capitalists and maintained 60% seven-day retention—impressive metrics for any bot.
But weather information is already one tap away on every phone. When Poncho tried expanding beyond forecasts to boost engagement, users lost interest. The company shut down in 2018.
Most chatbots never gain enough users to justify maintenance costs. Even popular bots struggle to become profitable.
In 2016, Duolingo created chatbots for its 150 million users to practice French, Spanish, and German without fear of embarrassment. Users could converse with Renée the Driver, Chef Roberto, and Officer Ada.
Duolingo never explained why these bots disappeared, though some users want them back. Real-time translation keeps improving—Skype already offers voice-to-voice translation—which may have made conversational practice seem less necessary.
Hipmunk worked on Facebook Messenger, Skype, and SAP Concur as a travel booking assistant. SAP acquired it, then shut it down in January 2020.
The team shared three lessons: Bots don’t need to be chatty—UI support works better. Travel bookings follow predictable patterns, simplifying intent recognition. Users prefer bots integrated into existing conversations rather than standalone bot chats.
Meekan used machine learning to schedule meetings in under a minute. Over 28,000 teams integrated it with Slack, Microsoft Teams, or HipChat. Users typed “meekan” followed by plain English instructions, and the bot checked calendars and set up meetings.
Despite analyzing 50 million meetings and clear popularity, Meekan shut down September 30, 2019. The company redirected resources to other scheduling tools, acknowledging the market’s competition made sustainable chatbot businesses difficult.
NYC launched an AI chatbot in 2023 to help small business owners. Investigations revealed it gave illegal advice, like suggesting employers could fire workers for reporting sexual harassment or sell unsafe food. Experts called the initiative reckles15 .
A New York lawyer used ChatGPT-generated case citations in a federal brief against Avianca. All the cases were fictitious. He faced potential sanctions when the fabrications came to ligh16 .
A study in Educational Philosophy and Theory found that over 30% of references ChatGPT cited in research proposals either had no DOIs or were made entirely up17 .
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Hello I'm Prof. Sakhhi Chhabra. I teach marketing subjects to post graduate students in India. I'm doing a research on chatbot user frustration and discontinuance. I would like to seek help in this respect that I would need data of users who have discontinued using chatbot. I would look forward to collaborating with you for this work. Do reply.
Hi there, thank you for reaching out. We unfortunately do not have user data, feel free to reach out to the chatbot vendors.
