lionz sorry, I should clarify, this is in regards to the current animations "Is Playing" value, specifically the one the debugger displays when inspecting the instance in question:
My understanding is that the debugger value is always updating to the current animation in real time, that is what it appears to be doing at least, and while "Is Playing" remains true most of the time, randomly it does turn false when switching to the attack animation.
Bandaid Solution in case anyone has this same issue in the future
While I have no clue what is setting this value to false and stopping my animation from playing, I was able to "fix" the problem by putting a "Start Animation from Current Frame" action after the "Set Animation" action.
To be clear, this shouldn't be necessary. The existing code works 95% of the time, but after adding this "Start Animation" action and running the game at 10x speed for an hour with an AI controlled enemy attacking a dummy, I haven't seen the issue pop back up. The debugger still shows the "Is Playing" value being set to false randomly, but this bandaid bypasses that.