AI agents are increasingly used in customer relationship management strategies to improve efficiency and reduce costs. Amid rapid advances in technology, the programs are becoming more human-like and versatile. However, AI agents with inadequate emotional responses can create an empathy gap, resulting in negative outcomes. If users' experiences fail to live up to their expectations, the resultant negative disconfirmation has damaging consequences for customers, the brand and the corporation. This chapter sets out the current types of human interactions with digital systems before examining the antecedents to negative outcomes, the three key types of negative disconfirmation and the consequences for areas such as brand engagement, AI agent trust and AI-induced brand hate. It then highlights that these harms are not inevitable, highlighting the mitigating action that firms can take to ensure their AI agents do not undermine their own customer relationship management efforts. Suggestions for future research are also provided.