I am trying to cut holes out of letters before cutting the perimeters of letters. However, with each hole, it appears to me that the tool is starting off cutting from the outside of the path, then moving to the inside of the path as would be expected with a hole.
Then, as it passes the entry point of the cut, it makes a sharp turn back to the outside of the hole.
It doesn’t act like it is catching or binding - it arrives at this location, then makes a deliberate turn to rejoin the original path.
In this first photo, you can see an example of this: The bit starts cutting a 10mm depth, goes all the way around the cut, and when it arrives back at the origin, it is now inside the original cut. It then makes a turn toward the outside, and cuts in perfect alignment the exact same path, repeatably.
In the next pictures, you can see that it’s doing this for all the holes in the file.