re: Insert / Path Hatching —› By Entity
It could be a workplane problem as Henry mentioned.
When I have several overlapping 2D objects, the first entity I pick with "By Entity" turns completely magenta. When I select the neighboring overlapping entity, the original turns off (I don't know why), but now I have a magenta line starting from where they overlap/intersect. Now I just need to select the next object near where it intersects with the previous object. The program will extend the magenta line to that click point. I repeat until I get back to where the magenta line begins. At this point, everything inside the magenta line should fill in with your specified hatch pattern.
Designer, Deluxe, (Professional, Expert, Basic), Platinum
Windows 10 Pro (1903), 64-bit