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Imagine a rogue PC sneaks into a room where a goblin -- who ought to be standing watch -- is instead taking a nap. The PC's stealth roll is enormously high (as befits a rogue), such that the goblin has no realistic chance of hearing the PC. The PC decides to attack the goblin.

In terms of game mechanics, what happens next?

Do both the PC and the goblin roll initiative? Or just the PC? Or no one? Or something else?

If the goblin does roll initiative, does it also instantly wake up? If so, why? If not, how could an unconscious creature even have initiative?

What if, based on the dice, the goblin wins initiative? How could that make sense given that the PC, whose attack would be the only conceivable cause of the goblin's suddenly awaking, hasn't acted yet?

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Since the goblin is sleeping, you could rule that the rogue surprises the goblin and gets a free round of actions before the goblin can react. In this case initiative is rolled as usual, but only the rogue gets to act on the first round (so if the goblin wins initiative, it still gets to act only after the rogue completes their turn).

Even if you don't rule that the goblin is surprised, it is unconscious and can't act on its turn, so the possibility of it winning initiative doesn't really matter that much. You should still roll initiative for it at latest when it wakes up (e.g. when it's attacked).

If not, how could an unconscious creature even have initiative?

Unconscious creatures having initiative is perfectly normal in D&D 5e. The usual case is a character reduced to zero hit points --- they fall unconscious and have to make a death saving throw whenever it's their turn in the initiative order. They still have a turn, just not much they can do on it.

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    \$\begingroup\$ Nice observation regarding a PC dropping to 0 hit points and nevertheless remaining in initiative. I hadn't thought of that. \$\endgroup\$ – screamline Dec 26 '18 at 15:29
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    \$\begingroup\$ Might be worth adding the unconscious condition text to this answer to really reinforce it. Point 1 covers it's complete lack of awareness and ability to move, and the fact that the creature is also considered incapacitated which means it can't take actions or reactions. \$\endgroup\$ – Lino Frank Ciaralli Dec 26 '18 at 22:08
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    \$\begingroup\$ there is no free round of combat in the rules. the surprised creature rolls initiative as normal, but doesn't get to act in the first turn. Some rogue abilities require the rogue to beat the initiative of the opponent. \$\endgroup\$ – Mindwin Dec 27 '18 at 11:40
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The answer to this is the combination of a few different rules, most which are found in the Player's Handbook ("PHB"), with a few extra notes found on page 77 of Xanathar's Guide to Everything ("XGE"), because these sort of questions did come up after the initial rules release.

First off, XGE makes its clear that when you're asleep, you have the unconscious condition (PHB p.292). So among other effects,

  • An unconscious creature is incapacitated, can't move or speak, and is unaware of its surroundings.
  • Attack rolls against the creature have advantage.
  • Any attack that hits the creature is a critical hit if the attacker is within 5 feet of the creature.

(The incapacitated condition merely says you can't take actions or reactions.)

Furthermore, there's surprise involved here (PHB p.189):

If you're surprised, you can't move or take an action on your first turn of the combat, and you can't take a reaction until that turn ends.

The rules given in XGE expand on this; in brief:

  • A sleeping creature wakes up if they take damage, if somebody uses an action to wake them by physical means, or if there is a sudden loud noise.
  • Your passive perception is not reduced for being asleep, and your passive perception determines how sleep-disruptive nearby sounds are (such as people talking or whispering).

So to pull it all together...

  • The Rogue's stealth roll is opposed by the goblin's passive perception.
  • Everyone in the fight rolls initiative, as usual. The unconscious condition doesn't say you can't roll initiative.
  • The goblin is unconscious until something happens to change that state, such as taking damage, and is surprised during their first turn in combat, whether they are awake or not at that point.

If the rogue goes first in initiative order and attacks the goblin in melee, they get advantage, sneak attack damage, and an automatic critical hit (if the attack hits). The goblin wakes up (assuming they aren't just dead at that point), but still can't take an action on their turn because they are surprised; but after that do-nothing turn (essentially spending their whole turn becoming un-surprised), they can take reactions, as they are no longer unconscious or surprised.

If the sleeping goblin won initiative, then it would be unable to act on the first turn (due to the unconscious condition); but after taking damage they would be awake and not surprised, thus able to take reactions immediately and able to act normally on their next turn.

If the rogue's stealth check had failed, then the goblin would wake up due to some noise, it would be up to the DM to rule whether the goblin is still surprised (most likely yes), and it would proceed much the same as if the rogue had failed stealth against any other target.

The DM might modify this.

It might seem odd that a sleeping creature is no easier to sneak up on than the same creature awake but inattentive (reading, talking, eating, or just standing around, for example). The DM might decide to give you advantage on your stealth roll against a sleeping creature to take that fact into account, but that isn't actually in the rules (which is fine, that's why we have a DM and not a Game-O-Tron 2000).

The DM might decide that the surprised effect doesn't start until the goblin wakes up, so even if it won the initiative roll, it would still have to go through one round of being surprised after being awakened by damage. That's not technically how surprise works, but it certainly makes sense in the context of this situation.

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Initiative rules are intended for situations where you need to simulate a two or more entities trying to act at the same time (typically while trying to murder each other). That doesn't sound like what is happening here. You have a player who is in a particular situation (standing next to a sleeping goblin) as a result of a choice he made (to sneak up on a sleeping goblin) and a die roll (he succeeds).

Rule 1 of all editions of D&D, and many similar RPGs: (which WotC fails to emphasize enough in their rulebooks for as important as it is) You, as the DM, are the central mechanic of the game. Your decision can override the Rules as Written at any time, and SHOULD do so when it makes sense for your game. When a player has declared a course of action and the intent behind that course of action, it is up to you to ask yourself some questions:

  1. Is it possible for the action to succeed, given situational factors and the player's approach? If yes, proceed to question 2. Otherwise, warn or inform the player and/or narrate the failure and tell the player to mark off expended resources.
  2. Is it possible for the action to fail? If yes, proceed to question 3. Otherwise, narrate the success and tell the player to mark off expended resources.
  3. Is there a risk or cost to failure? If yes, proceed to the normal action resolution mechanics (set DC, ask for skill check, mark off resources used, etc). If no, you can assume the player will keep at it until they do succeed, so you may as well just narrate a couple of attempts and keep the game moving.

It seems to me that your scenario breaks down at question 2: The rogue is standing next to a sleeping goblin. Your player says he wants to cut its throat while it's asleep. Its certainly possible for the action to succeed, but is there anything that would realistically allow a sleeping goblin to go from "Oh! There's a knife in my throat! I'd better try to defend myself!"? In the standard D&D world, I don't see it happening; that goblin is now stone dead as a result of the situation and the player's choices in that situation. This is the power of a game with a DM at the helm.

Same Scenario, But With a Dragon: Let's say your rogue is standing next to a sleeping adult dragon. Even with the element of surprise, it is not possible for the rogue to cause mortal harm to a dragon with just a little dagger before it can wake up, but Mr Bonehead McGigglemurder declares that he's going to try to slit the dragons throat. If, after you ask if he's sure that he wants to do that, he answers that he indeed wants to do that, let him deal his 1d4 + Dex Mod damage to the dragon. Since the dragon is presently asleep, you can even let it be a critical hit. Then the dragon wakes up and decides he wants to murder the rogue. NOW, and only now, is it time to break out the combat rules. Roll initiative and proceed.

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