As long as non-contact digital printing remains an uncommon standard in the corrugated packaging industry, corrugated board crushing remains a real issue that affects the load capacity of boxes. Crushing mainly occurs during the converting of corrugated board (e.g., analog flexographic printing or laminating) and is a process that cannot be avoided. However, as this study shows, it can be controlled. In this work, extended laboratory tests were carried out on the crushing of double-walled corrugated board. The influence of fully controlled crushing (with a precision of ±10 μm) in the range from 10 to 70% on different laboratory measurements was checked. The typical mechanical tests—i.e., edge crush test, four-point bending test, shear stiffness test, torsional stiffness test, etc.—were performed on reference and crushed specimens. The residual thickness reduction of the crushed samples was also controlled. All empirical observations and performed measurements were the basis for building an analytical model of crushed corrugated board. The proven and verified model was then used to study the crushing effect of the selected corrugated board on the efficiency of simple packages with various dimensions. The proposed measurement technique was successfully used to precisely estimate and thus control the crushing of corrugated board, while the proposed numerical and analytical techniques was used to estimate the load capacity of corrugated board packaging. A good correlation between the measured reduced stiffness of the corrugated cardboard and the proposed analytical predictive models was obtained.