This essay adapts the concept of “shitty automation,” developed by Brian Merchant to name frustrating experiences with automated systems, to describe how human input—our labor, bodies, biases, prejudices, and desires—remains invisibly present in automated systems. Tracing a lineage of automation from Jacques de Vaucanson’s Canard Digérateur (1739) and Wolfgang von Kempelen’s mechanical Turk (1770) to contemporary artist Trevor Paglen, who uses Generative Adversarial Networks (GANs) to create artworks, this essay considers how humans “stay in the loop” in automation and what “shitty automation” reveals about human culture, our desires, and the evolution of AI.