I think this situation is part of the dynamic of Tribunal that makes them fun to play at times. I can totally see Groggrom not flagging the imperials as long as they don't hit the Executioner.

A paladin on the other hand might have a different point of view. An evil might even invite them in to help. Imagine an evil tribunal inviting someone in to help and a good tribunal flagging the help. Oh, what fun!

Some Tribunals will flag if you flee in the wrong direction, others won't. It really is a matter of opinion. Of course, the Tribunal who does flag someone for entering in that situation would also be right.