When creating a extruded cut from a "surface/face/plane" with the direction "up to vertex" the order in which you select those two options changes the output. For example, if I select "extruded cut" -> "surface/face/plane" (Figure 1) -> "up to vertex" (Figure 2), the direction of the cut will be correct (from the surface, towards the vertex). However if I select "extruded cut" -> "up to vertex" (Figure 3) -> "surface/face/plane" (Figure 4), the direction of the cut will be incorrect (from the surface, away from the vertex).
I assume this is a glitch and I'm not doing something wrong? This issue is not a problem for a Extruded Boss/Base feature. Attached is the example file. I am using SolidWorks 2017.