Experiments on shock–shock interactions were conducted in a transonic–supersonic wind tunnel with variable free-stream Mach number functionality. Transition between the regular interaction (RI) and the Mach interaction (MI) was induced by variation of the free-steam Mach number for a fixed interaction geometry, as opposed to most previous studies where the shock generator angles are varied at constant Mach number. In this paper, we present a systematic flow-based post-processing methodology of schlieren data that enables an accurate tracking of the evolving shock system including the precise and reproducible detection of RI⇄ MI transition. In line with previous experimental studies dealing with noisy free-stream environments, transition hysteresis was not observed. However, we show that establishing accurate values of the flow deflections besides the Mach number is crucial to achieve experimental agreement with the von Neumann criterion, since measured flow deflections deviated significantly, up to 1. 2 ^∘, from nominal wedge angles. We also report a study conducted with a focusing schlieren system with variable focal plane that supported the image processing by providing insights into the three-dimensional side-wall effects integrated in the schlieren images.