Information Systems research on emotions in relation to using technology largely holds essentialist assumptions about emotions, focuses on negative emotions and treats technology as a token or as a black box, which hinders an in-depth understanding of distinctions in the emotional experience of using artificial intelligence (AI) technology in context. This research focuses on understanding employees’ emotional experiences of using an AI chatbot as a specific type of AI system that learns from how it is used and is conversational, displaying a social presence to users. The research questions how and why employees experience emotions when using an AI chatbot, and how these emotions impact its use. An interpretive case study approach and an inductive analysis were adopted for this study. Data were collected through interviews, documents review and observation of use. The study found that employee appraisals of chatbots were influenced by the form and functional design of the AI chatbot technology and its organisational and social context, resulting in a wider repertoire of appraisals and multiple emotions. In addition to positive and negative emotions, users experienced connection emotions. The findings show that the existence of multiple emotions can encourage continued use of an AI chatbot.