During 2018, as part of a research project funded by the Deviant Practice Grant, artist Bruno Moreschi and digital media researcher Gabriel Pereira worked with the Van Abbemuseum collection (Eindhoven, NL), reading their artworks through commercial image-recognition (computer vision) artificial intelligences from leading tech companies. The main takeaways were: somewhat as expected, AI is constructed through a capitalist and product-focused reading of the world (values that are embedded in this sociotechnical system); and that this process of using AI is an innovative way for doing institutional critique, as AI offers an untrained eye that reveals the inner workings of the art system through its glitches. This paper aims to regard these glitches as potentially revealing of the art system, and even poetic at times. We also look at them as a way of revealing the inherent fallibility of the commercial use of AI and machine learning to catalogue the world: it cannot comprehend other ways of knowing about the world, outside the logic of the algorithm. But, at the same time, due to their “glitchy” capacity to level and reimagine, these faulty readings can also serve as a new way of reading art; a new way for thinking critically about the art image in a moment when visual culture has changed form to hybrids of human–machine cognition and “machine-to-machine seeing”.