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This paper presents an overview of a complex approach to optimal planning of ancillary services ensuring reliable power balancing of a transmission system in liberalized market conditions that is performed by a transmission system operator (TSO). To accomplish this goal analytical computations together with optimizations and Monte Carlo simulations are performed. The designed decision support tool serves the TSO not only for a year-ahead planning task but also for carrying out various analyses and sensitivity tests, e.g., how costs of ancillary services are related to the level of reliability. Attention is also paid to mutual substitutability of ancillary services and its impact on transmission system operation and corresponding expenses.