D&D 5E Moving out of concealment to attack - when is stealth broken?

[clearstream]

You cease being hidden as soon as you leave your hiding spot and become visible to a creature (in this case, when you leave the darkness).

Unless the DM rules the monster you're sneaking up on is 'looking the other way'.

Once you make an attack from hiding you reveal yourself (hit or miss) after the attack is resolved, unless you have the Skulker feat and miss.

It's worth also noting that skulkers, and wood elves using Mask of the Wild, can be hidden in circumstances where they can see and target a foe - without having to step out of the hiding (seeing as their "cover" might be rain or dim light). I have found in play that these abilities make it very easy for them to attack from hiding.

 

[clearstream]

1) Does starting hidden allow you to stay hidden through your move....or is it the second you leave the darkness you lose the condition.

Unless the creature is distracted, it is as soon as you leave the darkness.

2) Assuming the answer to 1 is yes....once you make an attack, does that drop the condition of hidden....or could I still get the second attack with the benefits of being hidden?

Once you make an attack, that ends the condition of hidden. That includes the first attack of an attack action with extra attack. Some feats and features might change that, like Skulker.

 

[Reynard]

Not every round. Disadvantage kills SA outright. All the enemy near the Barbarian/Paladin has to do is dodge, that may or may not be a good choice but it will eliminate SA.

Depending on the initiative order the enemy can also use things like shove, movement or a ready action to kill SA. Again those may or may not be a good decision depending on the specifics.

Sure, but at least the fight becomes tactically interesting while they compete for advantage and disadvantages. At a certain level the tank spending their action to Help and make sure the Rogue gets SA off is probably worth it.

 

[DND_Reborn]

So the questions I am trying to nail down are:

1) Does starting hidden allow you to stay hidden through your move....or is it the second you leave the darkness you lose the condition.
2) Assuming the answer to 1 is yes....once you make an attack, does that drop the condition of hidden....or could I still get the second attack with the benefits of being hidden?

IIRC,

1. Another check would be required as soon as you move as otherwise movement reveals your location.

2. No, once you attack your position is revealed. The second attack is not from a hidden position either.

 

[DEFCON 1]

The real solution to all of this is this... if your DM is being stingy on sneaking up on monsters and stabbing them in the back... avoid making ANY melee rogues at all and just continually have ranged rogues firing bows out from behind cover, gaining Advantage and Sneak Attack often. You keep doing this over and over to the point where your DM gets so bored of that character concept that they end up coming on places like EN World to make the same tired "We need to nerf X because all my tables use X and it's so boring!" threads. (See the Great Weapon Master feat.) Then at THAT point you go to your DM and say "Look, if you want us to stop just using bow-firing rogues... then stop making it so hard for melee rogues to sneak up on monsters to stab them with Advantage and Sneak Attack just because you don't think it's 'realistic' to come out of the darkness and remain hidden!"

A "bored" DM is the best one to get changes made in your game. If they are going to be anal-retentive sticklers on what they think is the "right" way to play... then just play their way so hard and so often that they realize their "right" way to play can get very old very fast.

 

[auburn2]

The real solution to all of this is this... if your DM is being stingy on sneaking up on monsters and stabbing them in the back... avoid making ANY melee rogues at all and just continually have ranged rogues firing bows out from behind cover, gaining Advantage and Sneak Attack often.

I don't know if stingy is the right word. I would say the Rogue needs to do more than say "I sneak up on him". D&D is a story, if you are doing something that is not technically ok by the rules, tell me why it should be ok in this case.

 

[Reynard]

Rogues don't need advantage to sneak attack. I don't understand why making them work for advantage is considered a bad thing.

 

[Charlaquin]

The real solution to all of this is this... if your DM is being stingy on sneaking up on monsters and stabbing them in the back... avoid making ANY melee rogues at all and just continually have ranged rogues firing bows out from behind cover, gaining Advantage and Sneak Attack often. You keep doing this over and over to the point where your DM gets so bored of that character concept that they end up coming on places like EN World to make the same tired "We need to nerf X because all my tables use X and it's so boring!" threads. (See the Great Weapon Master feat.) Then at THAT point you go to your DM and say "Look, if you want us to stop just using bow-firing rogues... then stop making it so hard for melee rogues to sneak up on monsters to stab them with Advantage and Sneak Attack just because you don't think it's 'realistic' to come out of the darkness and remain hidden!"

A "bored" DM is the best one to get changes made in your game. If they are going to be anal-retentive sticklers on what they think is the "right" way to play... then just play their way so hard and so often that they realize their "right" way to play can get very old very fast.

Or just, you know, dual wield.

 

[Flamestrike]

Rogues don't need advantage to sneak attack. I don't understand why making them work for advantage is considered a bad thing.

Because it's time consuming having the Rogue roll Stealth each round and tracking which monsters he is actually hidden from, relative to the result.

It's why I love Tashas Aim action. No movement, bonus action, advantage on your next attack.

Quick, simple and deals with all these problems elegantly.

 

[Reynard]

Because it's time consuming having the Rogue roll Stealth each round and tracking which monsters he is actually hidden from, relative to the result.

It's why I love Tashas Aim action. No movement, bonus action, advantage on your next attack.

Quick, simple and deals with all these problems elegantly.

Advantage isn't intended to be that easy. Extra sneak attack damage is. If you combine them the rogue is significantly over powered.