What do glitches reveal about the normally invisible processes behind our interpretations? Glitches and Glitch Art illuminate the unseen assumptions, ideology of dialectical thinking, and role of established knowledge that shapes as well as determines our engagement with the world. Betancourt builds on the role of perception in guiding these interpretations to explore the possibilities offered by glitches for addressing digital media. Not confined to esoteric questions of semiosis, this study presents an expansive model of ambivalence and ambiguity whose ramifications address how initial assumptions and beliefs create meaning. Tracking glitches across technical media old and new, and moving from early abstraction's attempts to visualize a transcendental spiritualism through to contemporary AI generated art and media, Betancourt describes how glitches are not just technical failures but products of the instabilities between human interpretations and autonomous machinic operations that create a 'discursive aesthetic' guided by cultural fantasies of digital media's immateriality that idealize it as a perfect, transcendent form. A journey to the roots of meaning itself, Betancourt offers a paradigm that unpacks how engaging the glitch can become a critical model not only for artists, critics, and academics, but for anyone interested in Contemporary Art, tactical media, and cultural activism. all illustrations in full color