Blagoustroistvo is an archaic Russian word used today primarily to refer to urban public works. This article, a collaboration between an anthropologist and a historian, focuses on aesthetics, rhetorics, and concrete practices of blagoustroistvo in Moscow during two temporal junctures: the first decade following the October Revolution (ca. 1917–1930), and the decade of Sergey Sobyanin’s Moscow Mayoralty (2010–). Our juxtaposition reveals striking continuities and contrasts. Both in the 1920s and 2010s, we show, blagoustroistvo was characterized by a semiotically-intense presence in the city; associated with an emphasis on deterministic socio-psychological “engineering”; ideologically framed by a “vernacularized” form of Marxism-Leninism; and invested with a powerful role in reconfiguring society’s spatial hierarchies, political geometry, and class consciousness. In the former period, social transformation referred to the inversion of class hierarchies and a partly illusory reconfiguration of power between center and periphery. In the 2010s, however, blagoustroistvo became a project that sought a reversion to class categories and the re-colonial reconstitution of the center’s coercive domination of the fringes. Our analysis proffers blagoustroistvo—a high-modernist, deterministic “infrastructural ideology” that has endured into and flourished in the twenty-first century—as a uniquely illustrative concept for understanding the shifting ideologies of Soviet and post-Soviet infrastructural modernity and its winding but stubborn colonial logics. Moreover, our explication of blagoustroistvo’s trans-epochal meanderings brings comparative nuance to current global debates around the alleged “return” of “social engineering” to urban governance and design in the guise of artificial intelligence, big data, smart cities, and “surveillance capitalism.”