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In this study, a method is proposed for determining the maximum penetration level of wind farms (WF) based on permanent magnet synchronous generators and doubly-fed induction generators into the power system; it takes power system transient stability as well as frequency security criteria into consideration. Considering the probabilistic nature of wind speed, probabilistic transient stability analysis is introduced and applied to determine the maximum penetration level of WFs. The effect of overall system reduced inertia because of increasing capacity of WFs is investigated. A fast approach for deriving system frequency drop after a sudden disturbance is employed, which is suitable for online frequency stability constrained unit commitment incorporating WFs. The feasibility and effectiveness of the proposed method is evaluated using the IEEE 9-bus test system.