I'm A Banana
Potassium-Rich
I found the problem.
The Assassin has already declared the attack.
The attack is happening.
You can't go back in time and make the attack not happen. Further, the DM shouldn't be saying which NPCs won initiative. The DM should be narrating what the NPCs do.
The NPC when they lose initiative does nothing. The NPC win they win initiative does nothing. So they are indistinguishable. There is nothing for the DM to describe because the NPC isn't doing anything.
The only difference is that if the NPC wins initiative they might have a possible reaction to an attack. If that happens then the DM can say, 'okay Assassin, you have made your attack but your foe throws up the Shield spell (or whatever) at the last second.'
Yeah, this is not clear at all that it is RAI and it's definitely not RAW. There's no other place in the game where you don't get to decide your action on your turn. You don't even have to react to triggers for readied actions if you don't want to. Your adjudication is a solution, but it's one that significantly hoses an assassin player, makes an ambush a much less appealing tactic, and goes way beyond what the rules spell out ("forcing" a player to take an action that maybe they don't want to take anymore).
The alternative would be to roll initiative after the attack resolves, but that doesn't sound like it's RAI even though it'd be RAW, and it might make the assassin TOO powerful because they get two assassinate attempts.
A third option might be to use the Ready action out of combat ("I ready an action to snipe the guard as they come around the corner")...but that is basically the same as rolling initiative after the attack resolves, and potentially allows the assassin two assassinate attempts, still.
This is all part of why surprise is befuddling as frig and one of the major reasons that this is one of the rules changes that still trip me up.
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