D&D 5E Surprise and Sneak Attack

shadowoflameth

Adventurer
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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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

Hero
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

Patron Badass
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
Supporter
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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