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D&D 5E Surprise and Sneak Attack

So, here's a DM question. With a rogue and particularly, the assassin, this has come up. The surprise round is the first round of combat when one side is not aware of the threat. So, the assassin strikes with a sneak attack before the target acts and gets a critical hit. What about surprise after the opening round? If say, the assassin hits his initial surprise attack, uses cunning action to hide behind a wall or turns invisible, then attacks from a whole other direction with stealth. 'Where'd he go?' Surprise again? We have an assassin that can fly and at 12th level his stealth check is almost a sure thing. How do you handle surprise? What if he uses cunning action and gets out of sight without being spotted by the target when he attacks as he might with Greater Invisibility from the wizard, or with Minor Illusion? How do you rule on surprise?

In our game we use the optional flanking rule so advantage is fairly easy to get.
 

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Bayushi_seikuro

Adventurer
As a DM, my default assumption with rogues/thiefs/assassins since third-edition is that there should be a heavy use of wolfpack tactics. That a handful of rogues against a powerful enemy would be like a frenzy. Individually, rogues and their ilk are way less powerful - their strength comes from using these tactics to give the enemy the death of a thousand cuts
 



Teemu

Adventurer
Officially there’s no “surprise round” in 5e. You can be surprised, but that ends after your first turn, not first round. So if the assassin’s initiative is lower than an enemy who is surprised, the assassin can’t get the automatic critical hit against that target because the surprised condition ends before the assassin’s turn comes up!
 

MarkB

Legend
Officially there’s no “surprise round” in 5e. You can be surprised, but that ends after your first turn, not first round. So if the assassin’s initiative is lower than an enemy who is surprised, the assassin can’t get the automatic critical hit against that target because the surprised condition ends before the assassin’s turn comes up!
Which can get downright peculiar if the assassin is acting on their own. If the assassin decides to make an attack on an unaware target, initiative is rolled, and the target is surprised but gets a higher initiative than the rogue, can the rogue on their turn declare "actually, I've changed my mind - I'm just going to stay hidden for now", ending the encounter with no actions having taken place? And can they then declare "okay, this time I'm definitely gonna go for it", initiating a new encounter in the hopes of winning the initiative this time around?
 

Asisreo

Fiendish Attorney
Which can get downright peculiar if the assassin is acting on their own. If the assassin decides to make an attack on an unaware target, initiative is rolled, and the target is surprised but gets a higher initiative than the rogue, can the rogue on their turn declare "actually, I've changed my mind - I'm just going to stay hidden for now", ending the encounter with no actions having taken place? And can they then declare "okay, this time I'm definitely gonna go for it", initiating a new encounter in the hopes of winning the initiative this time around?
The rogue can decide to remain hidden but combat has been initiated and, since they are no longer surprised, they are aware of danger.

Maybe they've felt a gentle breeze when the rogue was preparing the strike. The rogue is still hidden, but the enemy may now have the urge to use the search action in the room, just to confirm their suspicions.
 

robus

Lowcountry Low Roller
There are actually two scenarios here:

1) The rogue/assassin has successfully got themself into a position where they can strike a killing blow. If the target is unaware and the rogue/assassin is not stressed by time then, if it would be reasonable for the target to die (assuming it’s not some behemoth monster they pricking with a short sword :) ), they kill the target. There’s no uncertainty to resolve with the rules.

2) The assassin/rogue as a member of the party has managed to get into a position to strike their opponents before they can fight back, but it is uncertain whether they can wipe out the opponents in that first strike. They gain the advantage of surprise and the combat plays out as per the rules.

Assassin‘s should be able to assassinate and not every aggressive action results in a combat encounter.

Edit: a missing not !!
 
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robus

Lowcountry Low Roller
Which can get downright peculiar if the assassin is acting on their own. If the assassin decides to make an attack on an unaware target, initiative is rolled, and the target is surprised but gets a higher initiative than the rogue, can the rogue on their turn declare "actually, I've changed my mind - I'm just going to stay hidden for now", ending the encounter with no actions having taken place? And can they then declare "okay, this time I'm definitely gonna go for it", initiating a new encounter in the hopes of winning the initiative this time around?

This is where I feel we misapply the rules. Remember the DM is the one that decides whether there is uncertainty in any situation. If a killing blow is struck is it uncertain that it would succeed? If yes, haul out the com bat rules, roll initiative and off we go. If it‘s not? Where’s the confusion? The target is dead.

We get peculiar results when we feed certain inputs into the uncertainty resolution mechanics . A person who should be dead is fighting back?! How did that happen? Because we brought in the rules before we asked if there was uncertainty to resolve.

Edit: jeez, autocorrect has been doing a number on my posts tonight. I demand satisfaction! Roll initiative you scurvy dog!
 
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The surprise round is the first round of combat when one side is not aware of the threat.

No, its not. There is no such thing in 5E.

So, the assassin strikes with a sneak attack before the target acts and gets a critical hit.

Not necessarily. Depends on who wins initiative in the first round.

What about surprise after the opening round?

Surprise is impossible after the first round.

If say, the assassin hits his initial surprise attack, uses cunning action to hide behind a wall or turns invisible,

So much wrong here as well.

then attacks from a whole other direction with stealth. 'Where'd he go?' Surprise again?

No.

How do you handle surprise?

I start by reading the rules on surprise.

In our game we use the optional flanking rule so advantage is fairly easy to get.

I hate that rule.
 

This is where I feel we misapply the rules. Remember the DM is the one that decides whether there is uncertainty in any situation. If a killing blow is struck is it uncertain that it would succeed?
1) The rogue/assassin has successfully got themself into a position where they can strike a killing blow. If the target is unaware and the rogue/assassin is not stressed by time then, if it would be reasonable for the target to die (assuming it’s not some behemoth monster they pricking with a short sword :) ), they kill the target. There’s no uncertainty to resolve with the rules.

2) The assassin/rogue as a member of the party has managed to get into a position to strike their opponents before they can fight back, but it is uncertain whether they can wipe out the opponents in that first strike. They gain the advantage of surprise and the combat plays out as per the rules.

Assassin‘s should be able to assassinate and not every aggressive action results in a combat encounter.

Edit: a missing not !!

Im going to hate this thread arent I?
 

Which can get downright peculiar if the assassin is acting on their own. If the assassin decides to make an attack on an unaware target, initiative is rolled, and the target is surprised but gets a higher initiative than the rogue, can the rogue on their turn declare "actually, I've changed my mind - I'm just going to stay hidden for now", ending the encounter with no actions having taken place? And can they then declare "okay, this time I'm definitely gonna go for it", initiating a new encounter in the hopes of winning the initiative this time around?

What @robus said:
1) If there is no uncertainty to the outcome of an Assassin making a deadly strike from the shadows, the DM should simply adjudicate that the Assassin kills the target. No attack roll necessary - and no initiative roll necessary for that matter. As DM, I would just ask the player to describe how the Assassin pulled it off.

2) If there is uncertainty in an Assassination attempt and as DM I called for initiative, I would not end the encounter just because the Assassin then opted to Hide instead of Attack due to losing initiative. The bolded bit above is false: initiative happened, combat began, and the Assassin chose the Hide action. Combat continues and the DM may want to start telegraphing a time pressure if one is not already there (e.g. "the sound of boots approach from down the hall...").


Side note: There are two parts of the Assassinate ability. You sometimes have one without the other and sometimes you can have both together in that first round of combat.
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.
 

Which can get downright peculiar if the assassin is acting on their own. If the assassin decides to make an attack on an unaware target, initiative is rolled, and the target is surprised but gets a higher initiative than the rogue, can the rogue on their turn declare "actually, I've changed my mind - I'm just going to stay hidden for now", ending the encounter with no actions having taken place? And can they then declare "okay, this time I'm definitely gonna go for it", initiating a new encounter in the hopes of winning the initiative this time around?

Th Rogue cant change their mind after they've declared an action!

Do you allow a PC to declare they're jumping over a pit, and then when they fail their Strength check to 'change their mind'?
 

What @robus said:
1) If there is no uncertainty to the outcome of an Assassin making a deadly strike from the shadows, the DM should simply adjudicate that the Assassin kills the target. No attack roll necessary - and no initiative roll necessary for that matter. As DM, I would just ask the player to describe how the Assassin pulled it off.

What If my sleeping Fighter at 20th level with 250 HP getting Assassinated?

Im just auto-killed am I?
 


Th Rogue cant change their mind after they've declared an action!

Do you allow a PC to declare they're jumping over a pit, and then when they fail their Strength check to 'change their mind'?

This is a fair point. If the player declared the Attack action, they shouldn't be able to pull it back after initiative is rolled. There are no guarantees to the Assassinate ability when the dice come out.
 

jgsugden

Legend
Note that a ranged assassin with a longbow can attack, break off and hide, then repeat the cycle by starting a new combat once the target tries to let down their guard to rest, heal, etc...
 

Lakesidefantasy

Adventurer
This has me thinking about the situation that often arises when, during a conversation with NPCs, a Player will declare surprise by attacking out-of-the-blue; however, if everybody is aware of each other they can't get surprise.
 

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