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The paper presents the results of a numerical analysis (FEM) describing the effect of the undercutting head angle on the formation of the rock mass failure zone during the initial stages of failure propagation. The research was carried out in the context of developing a technology for rock extraction by controlled pull-out of undercut anchors installed in the rock mass. The focus was on the initial stage of crack propagation and its trajectory for anchors embedded at an assumed constant depth and a value of the friction coefficient of the rock against the anchor head. It is shown that smaller angles favor smaller stripping angles and an increased radial impact of the head on the rock material (in the plane perpendicular to the head axis), while the impact of heads with larger angles is found to favor larger fracture penetration angles and faster penetration towards the free rock surface.