Chatbots are computer applications programmed to mimic human behaviour using machine learning and natural language processing. Chatbots can act autonomously and do not require a human operator. Given this freedom, chatbots do not always act in a manner that is fair and neutral – they can go wild with unintended consequences. For example, a chatbot “e-shopper” was given a budget of $100 in bitcoin and quickly figured out how to purchase illegal drugs on the Darknet. Another chatbot was programmed to mimic teenager behaviour using social media data. By the afternoon of her launch, she was firing off rogue tweets and taken offline by the developer. Chatbots were pulled from a popular Chinese messaging application after making unpatriotic comments. A pair of chatbots were taught how to negotiate by mimicking trading and bartering and created their own strange form of communication when they started trading together. Online dating sites can use chatbots to interact with users looking for love and increase user engagement. Chatbots can go rogue in chat rooms to extract personal data, bank account information, and stoke negative sentiment. Chatbots are increasingly being used by businesses as customer service agents. Even these legitimate and well-meaning corporate chatbots may also go wild.