Experiments reported in the literature are reproduced using numerical simulations to investigate the early stages of the breakup of water cylinders in the flow behind normal shocks. Qualitative features of breakup observed in the numerical results, such as the initial streamwise flattening of the cylinder and the formation of tips at its periphery, support previous experimental observations of stripping breakup. Additionally, the presence of a transitory recirculation region at the cylinder’s equator and a persistent upstream jet in the wake is noted and discussed. Within the uncertainties inherent to the different methods used to extract measurements from experimental and numerical results, comparisons with experimental data of various cylinder deformation metrics show good agreement. To study the effects of the transition between subsonic and supersonic post-shock flow, we extend the range of incident shock Mach numbers beyond those investigated by the experiments. Supersonic post-shock flow velocities are not observed to significantly alter the cylinder’s behavior, i.e., we are able to effectively collapse the drift, acceleration, and drag curves for all simulated shock Mach numbers. Using a new method that minimizes noise errors, the cylinder’s acceleration is calculated; acceleration curves for all shock Mach numbers are subsequently collapsed by scaling with the pressure ratio across the incident shock. Furthermore, we find that accounting for the cylinder’s deformed diameter in the calculation of its unsteady drag coefficient allows the drag coefficient to be approximated as a constant over the initial breakup period.