The increasing speed and ubiquity of imaging technologies pose numerous challenges to traditional distinctions between representation and reality. Yet, the role of the digital image as a medium is largely unexplored despite the significance of media and representations in architectural design and practice. Architectural images simultaneously proliferate and disappear. This thesis seeks to explore the medium of the digital image, arguing that its prevailing invisibility is concomitant with techno-utopian narratives constructing technology as an objective and autonomous driver of progress. Design research methods are used to reveal and trouble narratives embedded in digital images while also seeking counter-narratives through alternative computation design practices. Roosevelt Island, and its latest development Cornell Tech, serves as the site of study through its extended history as a site of urban experimentation and utopian projects. Images of the campus and Roosevelt Island are deconstructed to trace their formation and consumption, then manipulated and re-constructed towards counter-narratives of visibility. This research culminates in the design of an experimental re-appropriation of these images into an installation of a video-program series evidencing these findings, revealing the hidden agency in the materiality of the digital image.