This article focuses on how the recent proliferation of digital technologies in Nairobi, Kenya—a place many refer to as Silicon Savannah—is shaping the aspirations and anxieties of the city's poor. Taking as its point of departure an NGO project that enlisted settlement residents to digitally map their own neighborhood, I explore how geospatial technologies came to embody the shared dreams that animated Kenya's ambitious development plans and became implicated in debates about expertise, transparency, visibility, and truth. In particular, I discuss how utopian ideologies about technology, transparency, and mediation structured beliefs about the maps and map‐makers, and how the symbolic and material qualities of the digital form alternately enabled and challenged settlement residents’ self‐actualization. By foregrounding the ways in which subjectivity and social relations of power inform understandings of transparency, I suggest that settlement residents invoked transparency discourse as a form of claim‐making about technological expertise; through making their neighborhood visible through digital mapping, the mappers also attempted to make themselves visible as technical experts. In their struggle to become socially visible, however, the mapmakers’ status as technical experts was thrown into question. I argue that to see the inequalities (re)produced through technological imaginaries and sociotechnical engagements, we must analyze new media technologies as both potential vectors of sociopolitical recognition—that is, as technologies that make social relations of power visible—and as battlegrounds on which the urban poor's claims to transparency and expertise are affirmed or ignored, heeded or disregarded.