Tool-rock interaction processes can be classified as indentation or cutting depending on the direction of motion of the tool with respect to the rock surface. The modes of failure induced in the rock by an indenting or a cutting tool can be ductile and/or brittle. The ductile mode is associated with the development of a damage zone, whereas the brittle mode involves the growth of macrocracks. This is the first part of a series of two papers concerned with an analysis of the cutting and the indentation processes based on using the discrete element method. In this paper, numerical simulations of the cutting process are conducted to reproduce the transition from a ductile to a brittle failure mode with increasing depth of cut, which is observed in experiments. The numerical results provide evidence that the critical depth of cut d * controlling the failure mode transition is related to the characteristic length ℓ = (KIc ∕ σc)2 with KIc denoting the material toughness and σc its unconfined compressive strength. The nature of frictional contact between the cutter face and the rock in the ductile failure mode is also examined. It is shown that the inclination of the total cutting force is controlled by a multi-directional flow mechanism ahead of the cutter that is related to the formation of a wedge of failed material, intermittently adhering to the cutter. As a result, the inclination of the total cutting force varies with the rake angle of the cutter and cannot be considered an intrinsic measure of the interfacial friction between the cutter and the rock. Copyright © 2012 John Wiley & Sons, Ltd.