Okay, I've had some weird issues with the editor like that.
Try restarting it first. And then try it in the actual game.
Get back to me with the result and ill try to do some testing on it.
I know

(I always rebuild/reload after everything I do) It literally crashes my game once I click "End Dialog" as in, crash to desktop. That's both on a char thats set to global and a char thats not global. Both use different keyword dialog files etc... and yes, I checked "Leave" to "End Dialog"

on both of em.
I have literally managed to break my dialogs, completely. And I don't know why ;/