Processes that convert paperboard into finished products include, for example, printing, where the paperboard is subjected to rapid Z-directional (ZD) compression in the print nip. However, measuring and evaluating the relevant properties in the thickness direction of paperboard are not necessarily straightforward or easy. Measuring at relevant, millisecond deformation rates further complicates the problem. The aim of the present work is to elucidate some of the influences on the compressive stiffness. Both the initial material response and the overall compressibility of the paperboard is studied. In this project, the effect on the material response from the surface structure and the millisecond timescale recovery is explored. The method utilized is a machine called the Rapid ZD-tester. The device drops a probe in freefall on the substrate and records the probe position, thus acquiring the deformation of the substrate. The probe is also allowed to bounce several times on the surface for consecutive impacts before being lifted for the next drop. To investigate the time dependent stiffness behavior, the probe is dropped several times at the same XY position on the paperboard from different heights, thus achieving different impact velocities. The material response from drops and bounces combined allows study of the short-term recovery of the material. The material in the study is commercial paperboard. The paperboard samples are compared to material where the surface has been smoothed by grinding it. Our study shows that there is a non-permanent reduction in thickness and a stiffening per bounce of the probe, indicating a compaction that has not recovered in the millisecond timescale. Additionally, a higher impact velocity has an initial stiffening effect on the paperboard, and this is reduced by smoothing the surface.