re: did you use the Reach through mode on the countersink properties.
I tried all three "Reach" features. When I use Normal, TC shows a preview of the Hole before I select Finish. When I used "Through" and "Next Face", only the Point object lit up, but no preview of what the hole would look like. The Hole appeared when I selected Finish. I looked in Help, but they don't describe what "Through" and "Next Face" are or their differences. To me, they both do they same thing, which leads me to believe there is something broken here; I just don't know what.
After using Page Down, I click on the green highlighted "Face", then click on the Point to select that, then Finish.
Designer, Deluxe, (Professional, Expert, Basic), Platinum
Windows 10 Pro (1903), 64-bit