Digital government transformation is reorganizing public-sector work at a pace that civil service institutions have struggled to keep pace with. This article examines whether digital upgrading in Kazakhstan and Uzbekistan has produced a meaningful restructuring of the civil service workforce and why the translation of infrastructure investment into occupational change remains incomplete. The study draws on an asymmetric comparative design, combining shift-share occupational decomposition and vacancy-platform analysis for Kazakhstan with qualitative process tracing for Uzbekistan. In Kazakhstan, routine-intensive occupational shares declined over 2018-2024, yet persistent gaps in digital skill requirements and post-hire training suggest that formal restructuring has outpaced actual capability development. Uzbekistan shows a sharper version of the same pattern, where major digital and AI initiatives were launched before any consolidated reskilling architecture existed for the civil service core. These findings are captured through the concept of the reskilling paradox. Centralized personnel control, hierarchical information flows, and compliance-oriented organizational cultures act as friction coefficients that slow workforce adaptation regardless of how far digital platforms have advanced. Digital modernization, the evidence suggests, cannot be assessed solely through infrastructure.