The use of audio and textual chatbots, one type of digital intermediary, is pervasive and changing the way that we engage with computers and each other. Chatbots raise a wide range of legal and ethical issues, including questions about suitability for the user group, data collection, security of data storage and privacy, later linking of data, repurposing, as well as broader questions of accountability, applicable regulatory frameworks and responsibility to report, just to name a few. Chatbots, as benign as they first seem, raise a multitude of ethical and legal issues, questions and potential liabilities that need to be thoughtfully addressed. Adequate chatbots can be very easy to build – the more sophisticated the chatbot, the more technologically challenging- but both simple and complex chatbots require a certain level of technical and social complexity to maintain and dispose of.