In a discipline defined by its dialogue with images, methods, and cultural shifts, the introduction to this volume locates art history at a pivotal threshold: the emergence of intelligent technologies as both mirror and motor of disciplinary transformation. From the copperplate engravings in Winckelmann’s Monumenti antichi inediti to the brushstroke analytics enabled by contemporary machine learning, art history has long been animated by a restless engagement with the evolving tools that mediate perception, analysis, and dissemination. Today, generative platforms and computational systems extend this lineage, unsettling familiar habits while opening interpretive horizons. Yet, such technologies also surface anxieties—about the erosion of subjective interpretation, the authority of human judgment, and the ethics of data-driven knowledge—echoing earlier debates ignited by photography or the magic lantern. This introduction charts the evolution of art historical practice as a continuum of experimental adaptation, attentive to how cross-disciplinary currents from neuroscience to media studies have continually reshaped research, pedagogy, and public engagement. It offers a critical inventory of the assumptions, ambitions, and challenges that accompany this new technological inflection, foregrounding ethical stewardship and epistemological rigor as the guiding imperatives for the chapters that follow. In doing so, it invites art historians to view the computational turn not as rupture, but as the next dialogic stage in a tradition of methodological ingenuity, interpretive depth, and cultural responsibility.