Multi-dexel based material removal simulations provide a fast and flexible way to compute process forces and tool deflections for milling and turning operations. This allows an advanced process planning including detection of collisions for complex toolpaths. However, using dexel simulations for designing cutting tools has rarely been investigated. Especially the position of individual cutting edges is not considered, because current approaches only subtract the sweep volume of the tool envelop instead of the rake face. This paper presents a new method to design cutting tools using material removal simulations and a detailed tool geometry representation. The discretization of the tool allows an efficient calculation of the engagement conditions of individual cutting edges. The method is used to optimize novel porcupine milling cutters with round indexeble inserts, which produces a geometry analogous to serrated end mills. Based on the calculated forces, the positions of individual indexable inserts are adjusted to minimize the maximum radial force. An optimum has been found that reduces radial force by 12% compared to conventional porcupine milling cutters with squared inserts. © 2019 The Authors. Published by Elsevier B.V. Peer-review under responsibility of the scientific committee of The 17th CIRP Conference on Modelling of Machining Operations