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Modern power grids are composed of state-of-the-art equipment, increasing the importance of power quality assessment in such grids. Unlike synchronous machine (SM)-based pumped storage power plant (PSPP), doubly fed induction machine (DFIM)-based one has become a new trend for providing better support power system incorporating renewable energies. However, power electronic devices used in DFIM-based PSPP would increase the probability of occurring power quality issues, especially harmonics in voltage and current, which are assessed by the total harmonic distortion (THD) index compared to SM-based PSPP. This chapter intends to present the modeling, controller, and simulation of DFIM-based PSPP under generating operation mode. Then, the simulation study is designed in two stages for this chapter; In the former stage, the current and voltage waveforms of the DFIM-based PSPP are evaluated via fast Fourier transform (FFT) tools in MATLAB®/Sim-power. After that, the results of THD and the fundamental value corresponding to current and voltage are listed for generating mode. In the latter stage of simulation, the harmonic generation data of DFIM, extracted from the results of FFT analysis in MATLAB/Simulink, is used for the harmonic analysis toolbar of DIgSILENT PowerFactory. Simulation of this stage is conducted on a modified 10-machine 39-bus test system to assess the effect of DFIM-based PSPP on the power quality index of the power grid.