Cartography has long been framed as a central technology of Israeli state formation as well as a key medium employed to represent Palestinian dispossession. Rarely discussed, however, is how global digital platforms like Google Maps are transforming the terms through which Israel’s occupation is portrayed. This article examines how the use of Google Street View in Hebron, Palestine contests a colonial partition of vision. Tracking one Palestinian user’s employment of the platform—uploading user generated street-view images of a city otherwise occluded from Google’s maps—I delineate how Wesam’s impulse to “show his city” rubs up against Google’s claims to provide a purportedly object and neutral depiction of the landscape. Drawing from ethnographic fieldwork in Hebron and interviews with Wesam, I argue that, while what Wesam brings into view of the segregated city is severely curtailed by Israeli policies, his ability to make visible a reality of occupation on the ground forces us to reconsider the potentials of such extra-state digital platforms. Indeed, to move through Hebron with Wesam, users of Google Maps must pass through Israeli military checkpoints, Palestinian marketplaces covered with barbed wire to shield pedestrians from stones hurled by settlers, and backroads that circumnavigate partitioned roads. Building on Eyal Weizman’s articulation of Ground Truth, I ultimately argue Google Maps enables an alternative visual economy that brings the structuring effects of Israel’s occupation into relief.