This article examines the discourse of technological leapfrogging within dominant Asian development models—namely, the earlier manufacturing-led development (MLD) and the more recent services-led development (SLD)—which posit that developing nations such as India, China, and the Philippines are “catching up” with the West through digitalization, trade, and privatization of modern services. While these models highlight the shift from industrial production to Information and Communication Technology (ICT)-driven growth, they remain rooted in Western-centric modernization paradigms, assuming linear pathways to future progress, the efficiency of technocratic governance, and historical as well as institutional path-dependencies. These models, however, neglect the various “indeterminacies” of postcolonial development, overlooking how spatial asymmetries, historical contingencies, and socio-political contestations at multiple levels continually shape technological transformations across different societies. Challenging these normative assumptions, this article advances a Critical Postcolonial Political Economy (CPPE) approach, synthesizing insights from critical political economy, postcolonial and pluralist economic geographies. The CPPE approach centers on three analytical lenses: first, “social blocs” or the shifting coalitions of state, capital, civil, and political society actors that variously impact technological development and change; second, “plural temporalities” that reveal the non-linear, overlapping tempi of technology politics and development within national contexts; and third, “conjunctural thinking,” which parses technological transformations through moments of contestation, crises, and agency. Rather than prescribing yet another developmental blueprint, the CPPE approach seeks to demonstrate a decolonizing methodological praxis, disrupting grand global and regional narratives such as the “Asian miracle” and “Asian Century” that themselves universalize specific technological pathways to developmental ascendancy. Through situated histories and contested socio-technical transitions, the CPPE approach outlines a more politically generative lens for interrogating growth models across “incomparable geographies.” Ultimately, the article calls for rethinking technological leapfrogging beyond teleological assumptions, centering postcolonial indeterminacy in analyses of Asia’s (uneven) digital development.