In this thesis, I posit a conception of a specific subset of the Uncanny Valley of the Mind sensation that I call Uncanny Logic. A notion that was inspired by a passage in Adam Greenfield’s book Radical Technologies: The Design of Everyday Life detailing the experiences of discomfort by the spectators who witnessed the Go matches between Google DeepMind’s AlphaGo and Lee Sedol in 2016. This is done through a critical discussion of the current day technological reality of artificial intelligence as a field and its conflicts with the perception of artificial intelligence as an object of the uncanny. Via these discussions, I attempt to codify a tentative definition of the concept through analytic induction, which is thereby filtered through four alternating case studies. Two of these case studies are real-life events, and two are taken from fictional media so as to further illustrate the divide between current-day technological realities and perception with the cultural imaginaries of intelligent machines. Their insights are utilized to amend the final definition of the concept, which I claim will be of importance for understanding such complex feelings of unease in the future as our societies become further saturated with artificial intelligence-based technologies.