The electrical system of a wind farm has a significant influence on the wind farm reliability and electrical energy yield. The disconnect switch installed in an electrical system cannot only improve the operating flexibility, but also enhance the reliability for a wind farm. Therefore, this paper develops a probabilistic transfer technique for integrating the electrical topology structure, the isolation operation of disconnect switch, and stochastic failure of electrical equipment into the reliability assessment of wind farm electrical system. Firstly, as the traditional two-state reliability model of electrical equipment cannot consider the isolation operation, so the paper develops a three-state reliability model to replace the two-state model for incorporating the isolation operation. In addition, a proportion apportion technique is presented to evaluate the state probability. Secondly, this paper develops a probabilistic transfer technique based on the thoughts that through transfer the unreliability of electrical system to the energy transmission interruption of wind turbine generators (WTGs). Finally, some novel indices for describing the reliability of wind farm electrical system are designed, and the variance coefficient of the designed indices is used as a convergence criterion to determine the termination of the assessment process. The proposed technique is applied to the reliability assessment of a wind farm with the different topologies. The simulation results show that the proposed techniques are effective in practical applications.