Your avoidance moves are going through the part. Avoidance moves for holes are at the center of the hole at the distance away from the part that you type in. This is fine for an open hole in the part, but you are measuring a hole with a boss in it. You'll need to turn off avoidance moves and get into and out of the part another way. That is, you need to turn off the avoidance move and add a move point before and after the part, or do the same with a clearance plane.
I'm using 2021.2.. you can still add move points in between auto feature hits... show Hits=Yes... click the line you want the move point inserted after, click the x,y,z coordinates to bring up you move point dialogue box, then add the point.