This essay examines depictions of unreal architecture in the painting A Direct North General View of Sydney Cove 1794 (1793-5) (Sydney Cove 1794) contestably authored by the convict artist Thomas Watling. By comparing the painting to three of Watling’s topographic drawings, this essay demonstrates the repeated use of familiar architectural objects across these works and suggests the painting fragments an accurate representation of place—by assembling discontinuous visual information—to fulfil picturesque aesthetic principles. By considering various claims on the accuracy of topographic drawings—widely accepted as the authentic other to picturesque depictions—this essay challenges assumptions of their compositional neutrality. It argues that the same process of addition and omission of visual information is apparent in both picturesque and topographic depictions of architecture at Sydney Cove. Further, it claims that both types of image production depart from concerns of accuracy to satisfy familiar, although unreal, illusions of architectural civility, in an attempt to culturally assimilate a completely unknown reality. By linking these practices of image production to the emergent eighteenth-century culture of imitation, the painting is described as the consequence of an attempt to meaningfully represent unfamiliar land by using ideas of space and methods of depiction at a distance from their context. The result is the collapse of distance between depictions from metropole and antipode accompanied by an equivalent collapse between the mediums of image production and concepts of space. Sydney Cove 1794 portrays the experience of colonial estrangement by representing a space neither familiar nor foreign but dispelled from its centre through the endeavour of colonisation.