Images and anticipatory logic are intertwined. Humans have granted images the power to visually anticipate the future, which is traceable to the Palaeolithic but newly intensified in contemporary digital visual culture and platform economy. In this crosscurrent piece, we seek to interrogate the enduring and evolving nexus between images and anticipatory imaginaries and technologies, foregrounding what we refer to as anticipatory images: visual depictions of the not-yet with a performative effect in the present. We argue that images cannot be defined solely as representations of the outside world, as they also anticipate possible futures through acts of individual and collective imagination, thus acting out politics of temporality. Drawing on social theory on anticipation and visual culture and a selection of visual instances of anticipatory images, we highlight the sociocultural significance and role of anticipatory images as crucial analytical tools at the intersection of media studies, anthropology and social theory. Our aim is twofold: to reflect on how humans imagine and materialise anticipation through visual means and to unpack the politics embedded in contemporary anticipatory regimes by attending to visual culture, especially in the digital sphere, although not exclusively. Far from being confined to digital media, anticipatory images reflect a longer historical continuum of visualising futurity. Seeking to activate an interdisciplinary conversation, this piece calls for a more integrated scholarly approach to images and anticipation as co-constitutive forces in social life.