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I am trying to figure out if the surprised state ends on a creature after the first attack of a surprise round, or if the surprised state (which I would then see almost as an unofficial condition) ends only after the first round of combat.

In the second case, I would believe that a character (having the rogue's Assassinate ability) attacking a surprised creature AND having multiple attacks would score a critical hit on all hits.

Example: Does a Monk 5/Rogue 3 surprising a creature get automatic critical hits on all hits if he does 2 attacks (with extra attack) and additional unarmed strike(s)?

Or does the critical hit only affect the first hit? However, that would surprise me as the rules mention any hit is a critical hit.

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It's neither the first attack nor the first round. As far as RAW is concerned, if you're surprised, you're surprised at least until the end of your first turn. From the Player's Basic Rules, page 69:

The DM determines who might be surprised. If neither side tries to be stealthy, they automatically notice each other. Otherwise, the DM compares the Dexterity (Stealth) checks of anyone hiding with the passive Wisdom (Perception) score of each creature on the opposing side. Any character or monster that doesn’t notice a threat is surprised at the start of the encounter.

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. A member of a group can be surprised even if the other members aren’t.

The primary effects of being surprised last until the end of your first turn. It's not explicitly stated whether surprise ends when its effects end, but assuming the opposite would allow surprise to last for an arbitrary amount of time. If the duration of surprise isn't linked to the duration of the effects of surprise, we don't actually have any way to determine when surprise is supposed to end. So if the DM decides that you were surprised, you're surprised until the end of your first turn. Any attacks the Assassin lands on you before that will be critical hits.

For example: Alex the Assassin surprises Bob the Barbarian and Fred the Fighter. They roll initiative. Alex gets a 15, Bob gets a 20, and Fred gets a 10.

  • Initiative count 20: Bob's turn. Bob can't do anything, but at the end of his turn he is no longer surprised.

  • Initiative count 15: Alex's turn. Alex could attack Bob, but the attacks wouldn't be critical hits, because Bob is no longer surprised. Alex could attack Fred, and those attacks would be critical hits, because Fred is surprised.

  • Initiative count 10: Fred's turn. Fred can't do anything, but at the end of his turn he is no longer surprised.

  • Initiative count 20: Bob's turn. Combat proceeds as usual.

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  • \$\begingroup\$ Don't argue in comments. \$\endgroup\$ – mxyzplk Jun 7 '15 at 13:07
  • \$\begingroup\$ That's how it is written yes, but i have this doubt. dont know if i am supposed to make a new question or i can use this comment but here it goes. surprise is a 1st round, turn by turn "condition". it is tied to initiave, not awareness and i think thats the main issue. for example, an assassin is aware of the enemy but the enemy is not, roll initiative, enemy cant act on first turn, assassin is forced to attack then and there if he wants to use assassinate, thats nonsense to me. assassins stalk their marks entire hours before the killing blow, the surprise condition should be tied to awareness \$\endgroup\$ – Piero May 15 '17 at 6:56
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    \$\begingroup\$ @PieroManavella I think you might find this question useful - it's not the same, but it covers a very similar problem. If you find that doesn't cover your question, I'd definitely recommend asking a new question so that it can be answered properly. (If I try to answer you here, you're not going to get nearly as good an answer than if you ask it separately.) \$\endgroup\$ – Miniman May 15 '17 at 7:03
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@Miniman has answered this correctly but there still seems to be some confusion.

What an assassin can do (PHB p.97):

You have advantage on attack rolls against any creature that hasn’t taken a turn in the combat yet. In addition, any hit you score against a creature that is surprised is a critical hit.

What surprised is (PHB p.189):

Any character or monster that doesn’t notice a threat is surprised at the start of the encounter.

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.

So surprise has a start "the start of the encounter" and the effects of being 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") have a definite end - the end of your first turn.

It is nonsensical to claim that being "surprised" is a situation that can outlast the end of its effects; can being "unconscious" outlast the effects of unconsciousness?

Following the sequence of play on p.189 and using a very simple 2 creature example:

  1. Determine surprise: Alice the Assassin is not surprised; Victor the Victim is surprised.
  2. Establish positions: we will take that as read.
  3. Roll initiative: There are 2 possibilities:
    1. Alice rolls higher then Victor
    2. Victor rolls higher than Alice
  4. Take Turns

    1. If Alice rolled higher then Victor

      • Alice goes first and can: a) move out of Victor's reach secure in the knowledge that Victorwill not get an Attack of Opportunity - this is a reaction and Victor does not get them until after his first turn. b) use her assassin ability to i) attack with advantage because Victor has not taken a turn (this would be true without surprise and ii) get a critical on any hit because of surprise. If Alice has additional attacks and any bonus actions that grant attacks (e.g. Flurry of Blows or Two Weapon fighting) then this will apply to all of them.

      • Victor then takes his turn and "recovers from surprise".

    2. If Victor rolled higher than Alice

      • Victor takes his turn and "recovers from surprise"
      • Alice takes her turn and a) would allow Victor an attack of opportunity if she moves out of his reach - he can now take reactions b) cannot use either of her assassin abilities because: for i) Victor has had his turn and for ii) he is no longer surprised.
    3. Begin the next round

If Alice won the initiative then this combat is likely over. If Alice lost the initiative the only advantage she got from surprising Victor was not having him act in the first turn.

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  • \$\begingroup\$ @DavideMelfi: If Victor's surprised, he's unable to take reactions only until the end of his turn on the first round of combat. If Victor rolls higher on initiative, then by the time Alice can act, he can take reactions, including attacks of opportunity. \$\endgroup\$ – V2Blast May 23 at 1:32
  • \$\begingroup\$ So the way the rules work, for an Assassin (rogue) to actually surprise-attack someone, they also have to beat them on an initiative roll. This is sort of like a "saving throw" against being assassinated, and mechanically applies even when there was nothing to actually react to. (Just a crossbow bolt flying out of the night from behind.) But in a world where luck exists, sure. Related: What to do when surprise and a high initiative roll conflict with the narrative? \$\endgroup\$ – Peter Cordes Jun 7 at 5:52
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This is a very interesting question. It's easy to leap to conclusions about the actual situation.

I think the other answers are correct that once the surprised creature has had its turn, it's no longer surprised.

The reaction that this isn't right seems to be based on a couple of things:

  • Surprised isn't some condition so far as the rules are concerned. It seems to thematically represent the idea that the surprised parties must take a moment, however brief, to assess the situation before they can make any deliberate action. This doesn't necessarily seem to preclude them from making automatic reactions such as ducking or flinching due to some sudden movement.

  • That turns actually occur in the order they are played. This isn't really the case, the actions are supposed to be concurrent with initiative determining who is most able to react to the situation as it evolves.

  • That the surprise is occurring because the Assassin was hidden, and from there leaping to the assumption that whenever a target is surprised the Assassin should be able to carry out their full sneak + death attack. The latter is debatable - should an Assassin get death attack after kicking in a door on a room of surprised enemies then losing the initiative? Not necessarily, I think. In the case of the former, losing the initiative doesn't prevent the sneak attack, only the Assassin's death attack. Nothing to do with surprise or the assassin's death attack, but because you are an unseen attacker (PHB p195). Thematically, the target is just about able to assess the situation before the attacker strikes. They are still disadvantaged, but no longer in a state of surprise.

So for the moment I think the way I will play is as follows:

  1. Assassin strikes from in hiding - if the target loses initiative the attack gets both sneak and death attack bonuses on its first attack. If the target wins initiative, then the sneak damage still applies but not the death attack.

  2. Assassin kicks down a door and bursts in on an enemy. Typically this doesn't automatically grant advantage, but the enemy is still surprised. If the assassin wins initiative then they will get both advantage (due to Assassinate), sneak attack (due to the advantage granted by Assassinate) and the additional damage from Assasinate. However if they lose initiative, they will get neither - the target will no longer be surprised (and can in fact make reactions now) so Assassinate won't work, and without Assassinate granting advantage, neither will sneak attack.

I think this interpretation seems fairly logical and balanced.

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I believe you guys are misreading this.

Until the end of turn 1 and not the end of each person's turn.

You can do this two ways.

  1. If no one notices the Assassin, the Assassin gets his turn. Every hit from attacks would be crits on hits. Then round 1 starts and no one is surprised.

  2. Everyone rolls initiative. No one but the Assassin (or more if unnoticed) can move or act on turn one. Then start with the highest initiative on round 2.

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  • \$\begingroup\$ Welcome to the site! Please take the tour when you get the chance. It's important to note that we're not a forum, so answers should directly answer the question that was asked rather than attempting to reply to other answers. It looks like you have the core of a good answer here, but it's hard to tell because it's written like a reply to other answers. You can use the edit button at the lower left of your answer to improve it. \$\endgroup\$ – Oblivious Sage Sep 12 '18 at 20:03
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    \$\begingroup\$ @Marcus , you are incorrect. Fifth Edition D&D does not have surprise rounds. There is only the Surprised condition, which lasts from the start of the first round of combat to the end of your first turn. \$\endgroup\$ – lee A. Apr 27 at 16:40

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