The surprise round and you

So if the assassin then decides not to attack and remains hidden, can he declare "Combat Over" and then restart combat hoping to roll higher the second time around?

As I stated, initiative would actually get rolled until stuff happens. That stuff could include the assassin taking an action, or the guard suddenly noticing the creepy guy hiding in the bushes right behind him, or another guard walking out of an outhouse just in time to notice the creepy dude, or really anything.
 

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I think the rule is the way it is to protect the PCs from an attack by a hidden enemy outside of combat when the opposite situation happens, more than screw with the rogue.

That said, if you want to make the assassin rogue the exception to the rule, that seems like a fun option that I wouldn't argue against.
 

Based upon a recent Sage Advice and from the opinions of many people here on the boards... the answer would be 'Yes'.

Based upon the personal rulings of many other people here on these boards who find that situation to be the utmost in stupidity and who aren't afraid to actually let the Assassin character use his abilities... the answer would be 'No'. ;)

Let's turn it around.

The GM says to a player, "Your character takes *rolls* 37 points of damage."
.......... "How?"
"A stealthed assassin has hit you with a crossbow, that's critical and sneak attack damage."
.......... "Don't I get to roll initiative?"
"No, you were surprised."
.......... "That's not fair! Why don't I get to roll initiative?"
.......... "All right, I shoot the assassin."
"You can't."
.......... "Why not?"
"He used Cunning Action to Hide and then move away."
.......... "That's not fair!"
 

Let's turn it around.

The GM says to a player, "Your character takes *rolls* 37 points of damage."
.......... "How?"
"A stealthed assassin has hit you with a crossbow, that's critical and sneak attack damage."
.......... "Don't I get to roll initiative?"
"No, you were surprised."
.......... "That's not fair! Why don't I get to roll initiative?"
.......... "All right, I shoot the assassin."
"You can't."
.......... "Why not?"
"He used Cunning Action to Hide and then move away."
.......... "That's not fair!"


I always go with the "what's good for the goose is good for the gander" philosophy. What works for the PCs works for the NPCs exactly the same.
 

I always role for initiative after the action that initiated combat has finnished.

It's stupid otherwise. Only exception is "alert" feat, which is 5e version of 3e uncanny dodge. Then you may act before attack even.

an assassin with alert feat would sneak attack his ambusher if he rolled higher initiative because he gets advantage on attacks in the round that no one took action yet. But would not be able to assassinate as his ambusher isn't surprised.
 

My version:
Roll surprise - the assassin wins and the guard is surprised.

Roll initiative.

The guard goes first - he is surprised and does not get actions, however he will get his reactions past this point.

The assassin goes - he does not get advantage against the guard for going first, but he DOES most likely get advantage for being hidden. Since the rules do not say when "being surprised" ends (merely saying that you don't get a reaction until your first turn), I choose to interpret it as ending at the start of your first full turn. The assassin therefore gets his surprise bonus.

The guard gets his first full turn and is now no longer surprised.
 

So if the assassin then decides not to attack and remains hidden, can he declare "Combat Over" and then restart combat hoping to roll higher the second time around?

No. Initiative was rolled because the Assassin declared an attack. By choosing not to attack on his turn the Assassin is retconing that combat never took place because without his attack there is no need for initiative. To discourage this type of metagaming, I would retain the initiative rolls of the participants at least until after a new attempt at hiding has been made.

To be clear, I don't require actions to be declared in advance, but I discourage take-backsies.
 

Actually, there are a few solutions to the problem that are within the rules:

- give advantage to the assassin on the initiative check.
- let the assasin autowin initiative. It is a dexterity check and if the outcome is clear, you don´t have to roll.
(The assasin could start over and over again)

Those solutions have a flaw though: a multiclass fighter assassin will have up to 4 surprise attacks easily (extra attack feature, action surge)

A different idea is allowing the rogue(assassin) just to use a readied action to attack from surprise. Or give the assassin a free shot at the beginning of combat (no extra attack, no action surge possible) and then proceed with normal initiative. But I would then let everyone be not surprised anymore or allow for a new perception check to let them notice what has been going on against DC 10 maybe.

On the other hand, you must assume that surprise seldom happens actually. You are not surprised if you notice any threat. That is an assasin together with the usual plate wearer will never gets his surprise except when he is scouting way ahead. Just an attack from being hidden is no surprise attack.
So I would generally rule that as long as you are assuming a threat nearby, you can´t surprise someone. A guard that has reasons to assume danger right now is never surprised.
 

I replaced these new age suprise rules with the much more old school "I don't care if you got a 30 on your ini roll your suprised skip your turn.
 

On the other hand, you must assume that surprise seldom happens actually. You are not surprised if you notice any threat. That is an assasin together with the usual plate wearer will never gets his surprise except when he is scouting way ahead. Just an attack from being hidden is no surprise attack.
So I would generally rule that as long as you are assuming a threat nearby, you can´t surprise someone. A guard that has reasons to assume danger right now is never surprised.

I would still rule that the assassin gets his surprise if he beats passive perception with his stealth check. I do not care if a target spotted the metal plated tin can, he is still completely oblivios to presence of assassin and sees the knight as only potential threat.
 

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