Digitalization enhances regional competitiveness by optimizing resource utilization, fostering connectivity, and driving innovation. However, the long-term digital evolution of Russian regions remains poorly understood. The digital evolution is uneven and constrained by limitations in dynamic capabilities and digital human capital, often resulting in path dependency and development lock-ins. This study aims to identify the configurations of regional digital technology development and analyze their dynamic trajectories, which shape regional development pathways. We evaluate the interaction between pathways and the dynamics of human capital accumulation. Our approach combines evolutionary economics techniques, such as history-friendly modeling and compartmental methods, with formal statistical tools, including cluster analysis and regression. Using cluster analysis based on Rosstat data, the study identifies three groups of regions (progressive, inertial, and lagging) and their respective pathways from 2011 to 2022, including “leader”, “COVID impact”, “long disruption”, and “developing after 2014”. Pioneer regions, such as Moscow and St. Petersburg, demonstrate the “leader” pathway, having maintained high levels of digital maturity since 2011. The “long disruption” pathway, observed in southern regions, highlights persistent digital lag over the study period. Regression analysis reveals that regions following the “long disruption” pathway are characterized by insufficient basic digital skills and low innovation activity. The “leader” pathway is driven by the development of advanced digital skills, particularly in programming. The overall level of human capital positively influences region’s long-term digital performance. Practical implications include the need to differentiate regional development policies and increase attention to regions with a long disruption pathway.