Abstract In this paper the swept volume with self-penetration (or self-intersection) of the cutter is presented. The complete swept volume (SV), which describes the side and bottom shape of a milling cutter undergoing self-penetration, is generated by using the Gauss map method proposed in the authors’ previous paper [Lee SW, Nestler A. Complete swept volume generation—part I: swept volume of a piecewise C 1 -continuous cutter at five-axis milling via Gauss map. Computer-Aided Design 2011; 43(4): 427–41]. Based on the Gauss map method, the comprehensive analysis of envelope profiles of the tool is accomplished. Through the analysis the necessary condition of the self-penetration of the cutter at five-axis movement is identified. After having classified movement types of the milling cutter in an in-depth manner, the topologically consistent boundary of SV is generated by trimming the invalid facets interior to the SV. To demonstrate the validity of the proposed method, a cutting simulation kernel for five-axis machining has been implemented and applied to cavity machining examples such as intake ports of automobile engines and so forth where the self-penetration occurs. The proposed method is proved to be robust and amenable for the practical purpose of the NC simulation.