Quote: "Now segments have boundary's too, but does the 'cut' door allow the boundary for that segment to be changed? My guess is no since the overhead of the door is still part of the segment."
For DAI to pass through doors or arched walls you need a punch named 'Door' (even if the model already has the interior removed). This adds the path to AI outlines.
In custom media it may be that the depth of the punch is not meeting with the width of the room outlines. It likely is the editor if it worked fine before, for stock media at least.
To view outlines enable them in setup.ini, this way you can see where any issues are.
I don't trip over...I do random gravity checks.