The Arab Spring foregrounded a new reality that a digitally disruptive and highly networked world presents a wicked governance problem for governments seeking to enact effective governance systems in an era where citizen's unconventional digital mobilization can unseat repressive and unresponsive governments. This reinforces the need for spontaneous, contextually grounded and participatory e-governance mechanisms given their normative and transformative capacity to shift beliefs and norms of policy makers, enhance quality of policy outputs, elicit public confidence and heighten government's legitimacy. In this paper, the authors assess the efficacy of Uganda's e-governance policy, praxis and challenges as part of the broader e-governance discourse in the global south. The outcomes reveal that Uganda has instituted excellent legal, institutional and infrastructural e-governance mechanisms, but the conspicuous absence of political will, by an increasingly vulnerable political elite class, hampers sustainability of effective e-governance. Measures like rash and selective application of laws, introduction of new repressive laws, coercive means including violence and arbitrary arrest for dissenting opinions, increased state sponsored online and offline surveillance, internet shutdowns, network disruptions, online harassment, remote intrusion of civil society websites, and censorship, only further shrink civic space ultimately knocking both trust and legitimacy. Therefore, we propose that government prioritizes expansion of civic space to allow favourably reflexive and participatory citizen engagement as a pathway to enhanced quality of policy outputs and governance as a means to achieve its Vision 2040 by way of digital infrastructure, connectivity, legal and institutional frameworks and media freedom are dependent on political will.