We are confronted with a new type of uncanny experience, an uncanny evoked by parallel processing, aggregate data, and cloud-computing. The digital uncanny does not erase the uncanny feeling we experience as déjà vu or when confronted with robots that are too lifelike. Today’s uncanny refers to how nonhuman devices (surveillance technologies, algorithms, feedback, and data flows) anticipate human gestures, emotions, actions, and interactions, intimating we are machines and our behavior is predicable because we are machinic. It adds another dimension to those feelings we get when we question whether our responses are subjective or automated—automated as in reducing one’s subjectivity to patterns of data and using those patterns to present objects or ideas that would then elicit one’s genuinely subjective—yet effectively preset—response. This anticipation of our responses is a feedback loop we have produced by designing software that studies our traces, inputs, and moves. Digital Uncanny explores how digital technologies, particularly software systems working through massive amounts of data, are transforming the meaning of the uncanny that Freud tied to a return of repressed memories, desires, and experiences to their anticipation. Through a close reading of interactive and experimental art works of Rafael Lozano-Hemmer, Bill Viola, Simon Biggs, Sue Hawksley, and Garth Paine, this book is designed to explore how the digital uncanny unsettles and estranges concepts of “self,” “affect,” “feedback,” and “aesthetic experience,” forcing us to reflect on our relationship with computational media and our relationship to others and our experience of the world.