Cable-stayed bridges have become a major component of the Russian highway network over the past 25 years, and many of these structures are now approaching the stage at which long-term operational risks become critical. Experience from inspections, repairs, and monitoring has shown that cable systems are among the most vulnerable bridge components, particularly because corrosion- and fatigue-related defects may develop in zones that are only partially accessible to conventional inspection methods. This paper systematizes the Russian experience of operating highway cable-stayed bridges and presents a preventive, risk-based framework for cable-system operation that was used in the development of GOST R 59629—2021. This study is based on the analysis of 189 national and international regulatory and technical documents, the classification of cable systems relevant to Russian practice, and the structuring of operational measures across the design, construction, and service stages of the bridge life cycle. The proposed framework includes risk analysis at the design stage, formation of threshold and reference databases, integration of structural health monitoring, and condition-based planning of scheduled and unscheduled inspections and maintenance. The results support a transition from passive defect-response practice to preventive operations aimed at the early detection of pre-critical states and timely risk mitigation. However, major technical limitations remain, especially the incomplete non-destructive testing coverage of anchorage and transition zones, which constrains the reliability of condition assessment and should be treated as a priority area for further development.