This chapter explores some of the rhetorical and ethical issues in artificial intelligence (AI) as it intersects with professional communication. Zingle's parking service is a very bounded AI system, and even that one-task, one purpose system opens up considerable possibility for error and misunderstandings that impact the entire network of communication. However, of course, not all AI communication agents are designed from the outset for deception and manipulation. A large swath of the AI communication development is occurring for legitimate professional and personal uses, especially in the area of virtual assistants and their voice-activated control systems. Chat bots were no longer merely interesting curiosities for the general public and specialized research foci for AI researchers. Microsoft was widely public that Tay was an AI agent. Anyone who has used Amy will attest, and Mortensen acknowledges, that Amy, like most AI agents, is not perfect.