As our AI personal assistant devices develop human-like vocal accuracy, a new set of cultural, social, ethical, artistic and philosophical questions and implications begin to emerge. How such a technology might confuse and undermine voice-based verification systems? In an era of fake news, how does it complicate further existing cultural ideas about sources of information. How will users interact with the technology and what new creative processes, artistic responses and forms of sociability will develop from this interaction? How much will users trust it and what kind of new fears, paranoias will it inflict? This proposed project will research innovative methods by which the arts and humanities might address contemporary cultural processes about new forms of interaction between humans and machines as AI technology enters a new stage of vocal indistinguishability between them. The research methods will rely on a combination of art, design and computer science approaches. This will include an exploration of conversational AI models and the methodological role of multimodality and related forms of analysis in new kinds of communication interactions.