This article argues that, despite techno-utopian narratives of digital self-directed learning (through content freely available on the internet) and its proposed opportunities for upward social mobility, digital learning is and remains a highly contextual practice, rooted in local realities and aspirational trajectories. Through learning with a community-based organization (CBO) that offers tech training to youth from low-income neighbourhoods in Kibera, Nairobi, I argue that digital learning does not replace formal education but rather is strategically incorporated into already existing learning practices. Although Nairobi has been extensively studied as a frontrunner in technology uptake and development in Africa, it is crucial to also look at technology practices and uptake away from elite design and use, to extend and deepen our knowledge of how the digital realm plays out in the lives of the majority of urban residents.