Steels for sharp edges or tools typically have martensitic microstructures, high carbide contents, and various coatings to exhibit high hardness and wear resistance. Yet they become practically unusable upon cutting much softer materials such as human hair, cheese, or potatoes. Despite this being an everyday observation, the underlying physical micromechanisms are poorly understood because of the structural complexity of the interacting materials and the complex boundary conditions of their co-deformation. To unravel this complexity, we carried out interrupted tests and in situ electron microscopy cutting experiments with two micromechanical testing setups. We investigated the findings analytically and numerically, revealing that the spatial variation of lath martensite structure plays the key role leading to a mixed-mode II-III cracking phenomenon before appreciable wear.