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There are lots of questions posted about surprise and initative, but one scenario still seems ambiguous to me. If this has been answered, please link, as I couldn't find it.

Scenario: A player is stealthy in such a way as to make it virtually impossible to be noticed (invisible, rolls a nat 20 on stealth, opponent has very poor passive perception, etc.) and waiting to attack his unsuspecting opponent. When the player is ready to engage, the DM asks to roll initiative. Let's say the opponent rolls a higher initiative.

Surprise says that a surprised creature can't act on their turn but can make reactions after their turn. This reaction could potentially thwart the attack, making the surprise less effective.

Question: Knowing that the player won't go first, is there anything in the rules that prevent the player to just say to the DM, "Actually, I'd like to disengage from combat and continue waiting" in order to re-engage at some later time and re-roll inititative (which can be repeated for as many times as needed until the player gets a better initiative)?

Can the player go back from their decision this way to reroll Initiative or do they have to engage in the combat once Initative is rolled the first time?

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Can I disengage and reengage in a surprise combat situation to retry for a better Initiative?

No, but even if you could, it would be meta-gaming

When the player is ready to engage, the DM asks to roll initiative. Let's say the opponent rolls a higher initiative.

This is information your player character would not know ahead of time, or be able to react to. As it's a game, your DM may present this information to the players, but it isn't intended to be actionable information by the player characters.

Question: Knowing that the player won't go first, is there anything in the rules that prevent the player to just say to the DM, "Actually, I'd like to disengage from combat and continue waiting" in order to re-engage at some later time and re-roll initiative (which can be repeated for as many times as needed until the player gets a better initiative)?

By definition, the initiative order determines when you can act, so if you rolled lower than another creature, you cannot act until your initiative turn comes up. You could conceivably disengage or dash on your turn and attempt to leave the battlefield, but the opponent may choose to follow, continuing the battle, possibly becoming a chase. Surprising the same opponent moments later would be unlikely, but that's up to your DM.

Style

The DM's Guide gives a few options to DM's for how to handle initiative. Two of the three options keep the order hidden, implying you don't gain this information until each combatant has acted, and only if you pay attention. The other method provides the players with initiative order ahead of time, but this is pretty strong evidence this is not intended to be actionable information.

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By definition, Initiative is when the combat really starts

If surprised, a character or monster cannot act initially. But by definition, rolling Initiative is when the combat really starts, because Initiative is not relevant outside of combat, so at that time the victim of the attack is aware, that something is happening. No going back.

The victim can be more or less surprised. If the Initiative rolls are not in favor of the attacker, their surprise attack was less good than expected or the attacked was less surprised than possible. In reality you couldn't go back either once you had decided to make a move.

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    \$\begingroup\$ Okay so in essence, this is what happens? Player says I attack; DM rolls initiative; opponent gets a higher initative score, which takes its turn retroactively; then player continues the attack which technically started before initiative was rolled. \$\endgroup\$ Apr 3, 2023 at 16:41
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    \$\begingroup\$ Conceptually, if the opponent gets a higher initiative score and is not surprised, then the opponent has seen the PC starting to go for their blade (or cast a spell, or whatever) and reacted before the PC could actually attack. \$\endgroup\$ Apr 3, 2023 at 19:47
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Let's take this step-by-step. Fortunately, the rules do this for us.

This scenario has a PC (let's say "Pat") and an NPC ("Noel"). Pat is trying to sneak up on Noel. What happens?

Combat

COMBAT STEP-BY-STEP

  1. Determine surprise. The DM determines whether anyone involved in the combat encounter is surprised.
  2. Establish positions. The DM decides where all the characters and monsters are located. Given the adventurers' marching order or their stated positions in the room or other location, the DM figures out where the adversaries are--how far away and in what direction.
  3. Roll initiative. Everyone involved in the combat encounter rolls initiative, determining the order of combatants' turns.
  4. Take turns. Each participant in the battle takes a turn in initiative order.
  5. Begin the next round. When everyone involved in the combat has had a turn, the round ends. Repeat step 4 until the fighting stops.

Surprise

The DM determines who might be surprised. ...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.

The DM compares Pat's Dex (stealth) check to Noel's passive Wis (perception) score. In this scenario, Pat's check is sufficient that Noel "doesn't notice a threat" and, thus, "is surprised at the start of the encounter".

Positions are then established. Presumably, Pat is in an optimal position to attack Noel.

Initiative

When combat starts, every participant makes a Dexterity check to determine their place in the initiative order.

Combat starts when Pat's player declares the attack. If it occurred later than that, there's no way that Noel would be surprised (the dagger in their back would be a dead give-away); if it occurred prior to that, Noel's being surprised wouldn't matter (their first turn of the combat would already have passed). Remember that Surprise continues:

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.

Then, the normal combat loop starts: participants take turns in initiative order until the fighting stops.

If Pat rolls higher on their initiative check, they'll get two(!) whole turns before Noel can respond; if Noel rolls higher, Pat will still get the first action anyway: Noel "can't move or take an action" during their turn.

Remember, though: initiative is a real-world abstraction of the simultaneous events happening in-game. It's not like Pat moves and attacks then stands still for 6 seconds to see what Noel does; rather, Pat and Noel are both acting at the same time. Noel's surprise in the first round just means that their actions aren't combat relevant.

But what about that last bit of step 5: "Repeat step 4 until the fighting stops"? Doesn't that let Pat choose to disengage from the fight until they get a more beneficial initiative score? This GM says "no" because of the core game loop:

  1. The GM describes the world.
  2. The player describes what they want to do.
  3. The GM adjudicates the action and describes the new state of the world. If necessary, they use dice.

Pat's player's statement "I attack" means that Pat has committed to trying to attack Noel. The adjudication of that stated action is "combat begins; I've determined that Noel is surprised, so roll initiative then your attack".

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You misunderstand what’s going on here

The player has initiated combat - that is, they have done something so that combat is now inevitable. What they have not done is make an attack or cast a spell etc. because those things happen on the player’s turn and that hasn’t happened yet.

Think of the classic trope of the old west gunslingers staring each other down. Combat starts when one of them “reaches for it”, not when they fire. Or for an ambush situation, when the ambushers take aim or leap out of hiding or whatever fits the situation.

Once combat starts, surprise and initiative are determined. Those with quick reactions (high initiative) may beat the ambushers to the punch even if they are surprised.

Now, your character is committed to the combat but they are not committed to any particular action on their turn. That is, even though you might have intended to attack, you can change your mind and Disengage, or Dodge, or Cast a Spell, etc. when your turn rolls around.

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    \$\begingroup\$ @Dfvx990mq321pl "Combat is inevitable" here means that we have moved into the rules definition of combat - that actions are happening in initiative order. See the "combat step by step" sidebar. The steps there are: Determine surprise, Establish positions, Roll initiative, Take turns, Begin the next round. If you are in combat, you have to follow those steps - but nothing in those steps says you have to attack. In your case, the ambusher who lost initiative might well withdraw and try again, but that would be a different combat. \$\endgroup\$
    – Kirt
    Apr 4, 2023 at 2:32
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    \$\begingroup\$ @Dfvx990mq321pl combat is inevitable; specific actions aren’t \$\endgroup\$
    – Dale M
    Apr 4, 2023 at 6:13
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    \$\begingroup\$ @Dfvx990mq321pl “withdraw” is not an action AFAIK. The PC could attempt to get away; whether they succeed or not would have to be resolved. \$\endgroup\$
    – Dale M
    Apr 4, 2023 at 20:23
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    \$\begingroup\$ @Dfvx990mq321pl As Dale M said, the ambusher can try to get away - but this would be resolved in combat (meaning in Initiative order and with per-turn abilities). Also, even if they were successful, they might find the target more aware, less easy to surprise, and perhaps more accompanied the next time around. \$\endgroup\$
    – Kirt
    Apr 4, 2023 at 22:11
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    \$\begingroup\$ @JamesOtter I wouldn’t. \$\endgroup\$
    – Dale M
    Apr 5, 2023 at 21:05
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Initiative is a tool for the players and DM, the NPC doesn't know initiative has been rolled. They are simply unaware of the PC's presence and going about their activities. Initiative order will work like normal:

  • The NPC will do whatever they have been doing for their turn
  • The PC will take their turn, the NPC gets the surprised condition
  • NPC spends the next turn being surprised and gets access to their reactions at end of turn
  • PC takes their turn again
  • NPC takes a normal combat turn (provided they're still alive)

The player shouldn't have to disengage from combat unless they make themselves known for some reason at initiative 20.

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    \$\begingroup\$ I think this is how most people expect surprise to work, but not how the rules define it. The players don't get a free turn before the surprise round. \$\endgroup\$ Apr 3, 2023 at 16:48
  • \$\begingroup\$ @Dfvx990mq321pl I think this is the correct handling of surprise? It doesn't say that there is an extra round. It says that the surprised party is mostly unable to act which is correct I think. \$\endgroup\$
    – Anagkai
    Apr 3, 2023 at 17:15
  • \$\begingroup\$ @Dfvx990mq321pl I'm not claiming there is an extra turn for the players, I think you're drawing that assumption because there is one player and one NPC in this example. If there were multiple NPCs and players, then initiative would start (to matter) when the first PC acts and all NPCs would gain the surprised condition at the same time. \$\endgroup\$
    – Shadomew
    Apr 3, 2023 at 17:22
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    \$\begingroup\$ @Shadowmew Sorry, that is how I interpreted your answer and I am still not getting what else was intended with your example. Can you please clarify? In the example scenario, it says the NPC's surprise turn doesn't happen until step 3. That implies that step 1 was pre-combat and step 2 is a free PC turn. If that is incorrect, then what was your intent? \$\endgroup\$ Apr 3, 2023 at 17:29
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    \$\begingroup\$ This is not consistent with the rules for surprise. Surprise is determined at the start of the encounter, and surprised creatures can act normally after their first turn. The PC should only get two turns in a row like this if they roll higher on initiative. \$\endgroup\$
    – MJD
    Apr 6, 2023 at 19:30
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This may be unnecessary

Hopefully between the other answers, and some of the links I suggested, you have a better understanding of surprise, initiative, and how they interact.

But let's return to your original question - your ambusher has lost initiative; their target is still surprised, but now has a reaction available. Should you cease your attack? Has it been hopelessly compromised, so that your surprise is less effective? Or can you go ahead with equal chance of success?

The answer depends on the reactions available to them

Reactions:

Certain special abilities, spells, and situations allow you to take a special action called a reaction. A reaction is an instant response to a trigger of some kind, which can occur on your turn or on someone else's. The opportunity attack, described later in this section, is the most common type of reaction.

Note that you may only take a reaction when something allows you to. Each target will have access to different reactions, depending on their "special abilities, spells, and situations". Most targets will have access to an opportunity attack as a reaction - will this hinder your ambush? Well, it will have no affect on your attack itself - but it might affect what happens next. If your ambush was with a ranged attack, the fact that the target can use its reaction on an opportunity attack is irrelevant. But if you needed to close to melee, this could be important. If your attack did not incapacitate them, and they have a reaction available, they certainly could take an opportunity attack on you if you moved away.

Another common type of reaction is one that is used to take a Readied Action. This, however, you do not have to worry about at all. Because you surprised the target, they had no Actions on their first turn. Thus they were unable to Ready an Action and even though they have a reaction available on your turn, they will have no readied actions to use it for.

Beyond these two general types, the reactions available will depend on the specific target and what they have access to - three that you suggested were the Shield spell, a bard's Cutting words class feature, and a Battlemaster's Parry maneuver. Interestingly, some of these might make you call off your attack and others not.

Crucially, you have posited that your attacker starts their turn invisible. Now look at the description of Cutting Words:

Also at 3rd level, you learn how to use your wit to distract, confuse, and otherwise sap the confidence and competence of others. When a creature that you can see within 60 feet of you makes an attack roll, an ability check, or a damage roll, you can use your reaction to expend one of your uses of Bardic Inspiration, rolling a Bardic Inspiration die and subtracting the number rolled from the creature’s roll.

Notice that the bard can use this only on attackers that it can see. If you start the combat invisible, even if you are using the lowly second-level spell, you will be invisible until your initial attack hits or misses. Thus if your target is a bard, even if they have their reaction available, they will not be able to use their cutting words on your first attack, because they will not be able to see you. If you were planning on taking them out with a single attack, you have lost nothing by losing initiative. If you were counting on a second attack on your turn, such as with Extra Attack or a bonus action, that would be a different calculus. In that case, beating their initiative would confer an advantage, since they would not have a reaction available to use cutting words even though they could see your second attack.

Now compare this situation with the language of Shield, where the target can take their reaction:

when [they] are hit by an attack or targeted by the magic missile spell

and the parry maneuver, where:

When another creature damages [them] with a melee attack, [they] can use [their] reaction and expend one superiority die to reduce the damage by the number [they] roll on [their] superiority die + [their] Dexterity modifier.

Notice that these reactions are triggered by being hit (Shield) or damaged (Parry). In neither case does the target need to see you. Not all reactions are equal, and losing Initiative would be worse against some targets compared to others.

However, lest you think that this depends on your ambusher being invisible, be aware that the same consideration may be true if they are simply unseen. Refer to the Hiding sidebar in PHB Chapter 7:

In combat, most creatures stay alert for signs of danger all around, so if you come out of hiding and approach a creature, it usually sees you. However, under certain circumstances, the DM might allow you to stay hidden as you approach a creature that is distracted, allowing you to gain advantage on an attack roll before you are seen.

Depending on the circumstances of your ambush, even if you are not invisible and have lost initiative, you still might be able to approach your target unseen. Suppose you are approaching the target in a dense forest. You have a good Stealth roll; the DM determines that they are distracted (perhaps singing to themselves, composing their next ballad?) and surprised. You move at them from behind and enter combat; the DM instructs you to roll Initiative, and you lose. A bird sees your movement and takes to the wing; your target startles and now has their reaction - but they still don't see you moving up behind them until after your first attack. Bards beware!

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