This article presents a comparative assessment of digital transformation pathways in ASEAN economies, taking into account both the level and the structural composition of digitalization within the region. The study draws on internationally comparable data and advances an original temporal–taxonomic analytical approach based on the composite CMG indicator, which integrates three core dimensions of digital transformation: connectivity, market, and governance–sustainability-trust areas. The focus on Southeast Asian economies is substantively justified by the region’s pronounced heterogeneity in economic development, institutional capacities, and digitalization outcomes, combined with its strategic importance as one of the most dynamic emerging regions where digital transformation plays a pivotal role in shaping long-term growth trajectories and structural convergence prospects. The novelty of the research lies in the construction and application of the research tool: the CMG indicator—as a transparent and replicable measurement framework designed to enable the simultaneous analysis of the intensity of digitalization and its internal structure. Such an approach addresses key limitations of existing digitalization indicators when employed in dynamic and structure-oriented comparative research. Moreover, the integration of synthetic measurement techniques with cluster analysis allows for the identification of distinct digitalization profiles among ASEAN countries and for tracing their differentiated development trajectories under conditions of accelerated digital transformation. The results reveal substantial heterogeneity in digital transformation processes across the region, arising from the combined influence of differences in economic development levels, institutional conditions, market structures, and regulatory frameworks, which jointly shape national digitalization trajectories. The analysis identifies both advanced and relatively stabilized digitalization profiles, as well as catch-up pathways characterized by rapid improvements in digital infrastructure and regulatory environments. The conducted research demonstrates a clear value added resulting from the proposed coherent measurement framework, which enables the analysis of digital transformation from both temporal and taxonomic perspectives and provides new empirical evidence on emerging economies. The findings also have practical relevance, offering insights for the design of context-sensitive digital strategies aimed at reducing structural disparities and supporting inclusive and sustainable digital development in Southeast Asia.