Urban global waste generation has been growing at alarming rates and innovative sustainable solid waste management is considered vital to addressing the waste crisis. The vision to achieve this globally has mostly been taken its inspiration from cities in the Global North. Recently, these aspirations have merged with ideas of the “smart city” to integrate Information Communication Technology and digital systems to handle waste flows more efficiently through digitized large-scale infrastructure systems. However, the importation of a North- centric smart city logic into Southern cities has grappled with finding its “smartness” in the realities on the ground. Motivated by the need for more critical scholarship on Southern smart urbanism that explores the intersection of technology and urban infrastructural studies, this study uses participatory observation to investigate how digital technologies are used on the ground in the management of household solid waste in the neighbourhoods of Kibera and Mathare in Nairobi. In these self-constructed neighbourhoods with a long history in the city, participatory observations of household waste collection alongside semi-structured interviews with waste workers were carried out. Findings show how the practice of informal waster workers combine conventional digital technologies such as WhatsApp, Facebook, and the payment system m-pesa, with much more mundane technologies of barrels, carts, and saving schemes to carry out their job and earn a living. In comparing this with the official smart city discourse in Nairobi, a great disconnect between how smart solutions to waste management are envisioned and how it plays out at the grassroot level. The thesis argues for grounding smart city discussions in the global South in lived realities. Rather than “smart,” a case is made for “street smart” or shrewd urbanism that could enrich the understanding of how digital technologies are being worked into the city fabric in cities of the South.