This article describes a proposed procedure for multiparametric optimization of the quality of machined surfaces, including mathematical models that can predict the high quality of a precisely machined surface and, at the same time, the high productivity of the process in WEDM of tool steels. The experimental research was carried out using the full DoE factorial design method, which has four technological parameters. The measured output qualitative parameter Surface Roughness (SR) and the output quantitative parameter Material Removal Rate (MRR) were evaluated using the Grey Relational Analysis (GRA) and Analysis of Variance (ANOVA) methods. Multiple Regression Models (MRM) were developed to represent the multiple responses of the investigated tool steels using a regression tool set. The results of the multiparametric optimization revealed a correlation between the input variable parameters of the electrical discharge process, while the favorable results of the observed output-dependent parameters SR and MRR were coupled to the parameters of low peak current I, low value of pulse on-time duration ton, low voltage of discharge U, and high value of pulse off-time duration toff. Based on the multiparametric optimization, key results were obtained that demonstrated the mutual dependence of the observed output process parameters. An optimum SR value of 1.50 μm was obtained with L8-level settings for the input variable parameters I, ton, U, and toff (2 A, 32 μs, 90 V, and 20 μs, respectively) and an MRR value of 12.50 mm3·min−1 was achieved.