This thesis interrogates the paradoxes of digital transformation in Nigeria's agri-food supply chains, with particular focus on tomato production. While digital technologies are widelypromoted for their potential to increase efficiency, reduce food loss and waste, and enablemarket access, their real-world performance in resource-constrained contexts often falls short of these promises. Against staggering post-harvest losses, with up to 50% of fresh tomatoproduction wasted before consumption, this study asks a fundamental question: Why do digital interventions in agriculture often fail to deliver their intended outcomes, and under what governance conditions can their performance be enhanced? The inquiry is situated at theintersection of development economics, institutional theory, and digital transformation studies. Drawing on a critical realist philosophy and an abductive research design, the study synthesises insights from two systematic literature reviews and 79 in-depth interviews acrosstwo contractually distinct cases of tomato production: government-led and donor-drivenproduction hubs, and private-led venture-backed commercial innovation platforms. Using theGioia method for thematic coding, the research surfaces five paradoxical constraint mechanisms characterising digital transformation in agri-food systems: Constrained Efficiency, Fragmented Formalisation, Disrupted Informality, Residual Governance, and Algorithmic Mistrust. These paradoxes reveal a counterintuitive insight: digital inefficienciesare not simply products of infrastructural deficits or behavioural inertia but are often embeddedwithin incomplete contractual architectures, fragmented institutional environments, and asymmetrical governance logics. This insight culminates in developing the Digital ConstraintParadox (DCP) Framework, a novel conceptual typology mapping the interaction between institutional support and resource capabilities in shaping digital outcomes. Theoretically, this dissertation advances an extended governance-based theory of digital transformation by integrating paradox theory, institutional logics, and incomplete contract theory. This study repositions digital transformation as a terrain of contestation, where efficiency is neitherautomatic nor apolitical, but a negotiated outcome shaped by governance, trust, and theinvisible architectures of constraint.