This article presents advances in the methodology of rapid various probe configurations comparison for the five-axis, tilting-head machine tools in conjunction with master artifacts. The research was performed in a direct context of automated machining of large, complex jet engine cases made from 17-4PH and 321 stainless steel materials. The aim of the study was to investigate whether all probe configurations have comparable measurement capability for use in manufacturing environment conditions. Based on the preliminary stage of the study, the T1 main straight probe achieved acceptable results of repeatability and reproducibility, lower than 10%, except for the reference diameter measurement of MT#2, where 15.4% R&R was achieved, conditionally accepted. For the straight probe configuration, error lower than 10 μm was achieved for the true position measurement and error ±10 μm for the reference diameter measurement, in relation to the vertical and horizontal head position, with the exception of the T9 and T5 MT#2 probe configuration, where higher error was noticed. The obtained results of the T5 MT#2 and T9 probes were supplemented with additional tests, which are also included. For the custom styli probes, the T4 and T6 configurations, unacceptable error, higher than 0.30 mm, was observed for the Y axis position. Depending on the shop floor and machine tool condition, variability of the results was also observed. Hence, the collected data and research helped to determine the mutual measurement errors and determine the application limitations of probes for an adaptive process flow.