Stories about smart cities borrow from techno-discourse a tendency towards placelessness that works to obscure the irreducible specificity of the urban. In these blog entries I will focus instead on a very specific site: Pittsburgh, the city where I live, and whose ongoing history of post-industrial decay and technological reinvention looms large in the imaginary of the smart city. With Pittsburgh as both a subject and site, these blogs aim at delivering a few short historical, speculative, and personal sketches aimed at situating, unsettling, or playfully reconfiguring the fantasies of prediction and control that underpin smart city ideology.