Can a Gloom Stalker ranger continuously use Dread Ambusher if they knock-out or eliminate enemy after enemy, as long as it happens in one turn?

Question

In D&D 5e, if a gloom stalker (ranger) is infiltrating somewhere while in stealth. Would it be possible for them to attack one enemy, potentially eliminate them, re-enter stealth and proceed to do that with other enemies, as long as they stay hidden?

A player is playing a Ranger/Monk/Rogue multiclass, and wanted to know if it would be possible for them to: Attack unseen with Attack Action (2 attacks) -> Dread Ambusher Attack -> Bonus Action Attack (Monk Martial Arts - As long as they are using monk weapons or unarmed). Then proceed to re-enter stealth and take out other enemies in the same fashion.

They are considering that they would be taking out each enemy on their 1st turn. That would make it multiple combats. For example, let's say they take someone out in a single turn. Try to Hide, turn a corner and try to take someone else. That's their query.

It does sound like it should work like that, but I rather ask to be sure as I'm a little uncertain about this particular mechanic.

Thank you.

Answer 1

It can't all happen on one turn

As your Action, the character takes the Attack action, so, as a high enough level Ranger, they can get two attacks. As a Gloom Stalker, so long as it's the first turn in combat, you can also attack one extra time as a Dread Ambusher. And that's your Action.

As your Bonus Action, assuming you are attacking with monk weapons or unarmed, you can attack a 4th time. Alternately, with Fury of Blows you could make a 4th and 5th unarmed attack.

But that's it.

You cannot "re-enter stealth" in that same turn as you've used up all your actions/bonus actions. So if you killed/rendered unconscious the ONE enemy. You can out of combat try to hide again and move on to the next enemy.

But anyone can do that

There is nothing stopping a fighter, cleric, or wizard from offing a single enemy in one turn so they can hide and move on to the next enemy. So long as they can all be approached singly.

From your description, it sounds like you expect a room full of enemies that you can hit, take out, and hide from one one-at-time, without any of the other people in the room figuring it out. Which as I pointed out, cannot all happen in one turn.

If you managed to take them out with just your attacks/dread ambusher, you can as a rogue use your bonus action to try to hide again. But unless you're amazingly stealthy, someone is going to hear you.

How long is combat is up to the DM

I noticed you added a little more detail.

If the DM set up the encounter where there is only one enemy at a time, then (a) yes, as pointed out, each combat would allow a "first turn" special bonus attack, and (b) your DM really needs to work on how to set up encounters.

You are at minimum 7th level (5 Ranger, and 1 each Monk and Rogue). Many characters are getting multiple attacks. Having multiple isolated creatures in a row (around corners, through a door, etc) is just bad planning.

But even then, just because a creature is "around the corner" doesn't automatically mean it's a new combat. I've have many sessions where the party would take out what they thought was a single creature, but the noise caused more to rush in. Sometimes with a round in between for us to "prepare"; same combat, but just a freebie round.

So the scenario you described could work, but I wouldn't count on making it a standard operating procedure.

Answer 2

You only can re-use Dread Ambusher after you leave combat

The description of the Gloom Stalker ranger's Dread Ambusher feature states, in part (XGtE, p. 42; emphasis mine):

At the start of your first turn of each combat, your walking speed increases by 10 feet, which lasts until the end of that turn. If you take the Attack action on that turn, you can make one additional weapon attack as part of that action. If that attack hits, the target takes an extra 1d8 damage of the weapon's damage type.

During that first turn, you can attack and kill several enemies with your attacks if they deal enough damage. However, once you are engaged in combat, you cannot use Dread Ambusher on subsequent turns, hidden or not.

Attacking breaks Stealth, DMG p 195:

If you are hidden--both unseen and unheard--when you make an attack, you give away your location when the attack hits or misses.

So unless further enemies are somehow positioned in a way that they would not perceive the first attack — and that’s not easy because perception includes listening, too - they will notice it and you will be in combat after you attack, even if you manage to hide again.

It will be up to your DM to decide when combat ends. The "Order of Combat" section of the rules says (PHB, p. 189):

Once everyone has taken a turn, the fight continues to the next round if neither side has defeated the other.

So, unless you sneak entirely away from combat, your DM is justified to rule that combat has not ended as long as enemies remain.

The Dread Ambusher attack is part of your Attack action, not separate from it. After using your action for the Attack action (and possibly your bonus action for another attack, if you have something that allows this), you’ll be out of actions for your turn (barring maybe a reaction). You can still move, but that’s it.

Hiding takes an action too, or at least a bonus action if you are a rogue. If you already used both when you executed your private little massacre, you cannot hide again in the same turn.

Answer 3

Yes. If the enemies fail their perception checks to notice the character's actions.

If a character successfully attacks and kills someone without their friend in the next room realizing, that friend has not entered combat. There is no magical 'i'm in combat' sensor in D&D 5e. Combat starting and entering initiative only occurs once hostile creatures become aware of each other, often due to some action taken by one or the other or simultaneously. If a creature is unaware of an enemy, they will be Surprised and that enemy will gain a surprise round, otherwise both roll for initiative if they become simultaneously aware of each other.

It is up to the DM to determine whether a creature is aware of environmental noises and thus deduces the presence of an enemy. If it is simply to detect the presence of a Hiding creature, it is Stealth opposed by Perception, or passive perception. However things like 'the dying gurgle of a guard who has been stabbed in the throat' may influence these numbers (if the character is trying to, for example, muffle the dying gurgle by placing their hand over the dying guard's mouth) such as by providing some kind of bonus to the creature's Perception check, or having the creature compare to a flat DC rather than be opposed by the character's stealth (does the kobold guard hear his buddy fall over and pick up his spear and come investigate? let's see).

Which of these the DM uses is not particularly indicated by the text, and will likely be up to the DM to determine on the fly, likely depending on situation and the character's actions.

Narratively, this is perfectly in theme for any number of fictional characters. 'Wiping out the guards one by one' is a time honoured trope for any kind of stealthy character. In many movies, books, etc this occurs and often several individuals are taken out before any kind of alarm is raised. This is something that also occurs in real life - it's a big concern in security design and military planning alike, even in the modern age.

This does make the Gloom Stalker's Deadly Ambush feature considerably stronger in these sorts of 'isolated battles', and it's not exactly a weak feature to begin with. Therefore, if the Gloom Stalker is taking too much of the spotlight time with their assassination tactics, consider rewriting some encounters to have enemies in closer proximity, with more awareness of each other, or using methods such as tripwires, alarm spells, or watchdogs to detect sneaky threats. These are all very reasonable measures in a world where enemies can go invisible and mimics want to eat you, and not too much of a nerf to the gloom stalker's effectiveness, as they are still likely quite potent in regular combat.