Does the Gloom Stalker ranger's Dread Ambusher feature grant a separate attack?

Question

I'm currently playing a game in which I am running a Gloom Stalker ranger with the dual fighting.

The Dread Ambusher feature gives me an additional attack with 1d8 damage. At this point I have my main attack, my off hand attack, my extra attack (gained at level 5), and the Dread Ambusher attack for the first interaction in combat.

The way my DM interprets this is that with my first attack the Dread Ambusher is included in this attack like doing additional damage when pulling the blade out sort of thing. This essentially makes the extra attack from Dread Ambusher useless if the creature I attack dies with my initial attack.

I have three attacks anyways but I'm curious if Dread Ambusher is a separate extra attack or if it is a part of the initial attack as my DM says. Of course if that's the way he plays it that's fine, but I'm looking at running my own campaign and want to make sure I am running this correctly for my party.

Answer 1

You get 1 additional attack, if you take the Attack action on the 1st round of combat; it does 1d8 extra damage (plus normal weapon damage) if it hits

The Gloom Stalker ranger's Dread Ambusher feature (Xanathar's Guide to Everything, p. 42) says, in part:

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.

Taking it step by step:

It only applies on your turn on the first round of combat.

• It doesn't apply on subsequent turns of that combat, i.e. until you reroll initiative (which is generally what mechanically distinguishes one "combat" from the next).
• Your walking speed increases by 10 feet (e.g. for a human with no other speed bonuses, it goes from 30 feet to 40 feet) only until the end of that turn. This has no relevance to attacks (other than potentially getting you within reach/range to make them), so I'm ignoring it in this answer.

It only applies if you take the Attack action on that turn.

• If you use your one regular action to cast a spell, or Disengage, or anything besides the Attack action, it has no effect.
• If you multiclass into fighter for the Action Surge feature, though, you could potentially take two actions that round - and if you do take the Attack action twice that round, you would get to make the additional attack twice that round: once for each Attack action. (This "exploit" is not possible with the haste spell, which limits the number of attacks you can make with your new action from the spell if you take the Attack action.)

If you're able to make that additional attack on the Attack action, and you hit, you do 1d8 extra damage with that attack.

• If the additional attack misses, you don't do the extra damage. Simple.
• Note that no general rule restricts the order in which you make the attacks in an Attack action - and nothing in the feature specifies when during your Attack action this "additional weapon attack" must be made. As a result, it's up to DM discretion how it's determined which attack gets the extra damage. Presumably, which attack is your additional attack (from Dread Ambusher) must at least be decided before the attack is made, so that you can't simply wait until you hit in order to guarantee that you get the extra damage, but naturally your DM can rule otherwise.

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No special interaction with Two-Weapon Fighting

This feature has no interaction with Two-Weapon Fighting, or your bonus action. If you make an attack during your Attack action that qualifies for TWF (i.e. you make at least one - any one - of the attacks in your Attack action with a one-handed light weapon), then you can use your bonus action to attack with a one-handed light weapon in the other hand, as the TWF rule states. There's no special interaction between the two, other than that you have one more attack in your Attack action with which to qualify for TWF.

A 3rd-level ranger wielding two weapons that qualify for Two-Weapon Fighting can normally make 1 attack during their Attack action, and 1 bonus-action attack from TWF. Dread Ambusher lets them make 1 more during their Attack action on their first turn, for a total of 3 attacks; for the rest of the fight, they go back to 2 attacks per turn.

A 5th-level ranger wielding two weapons for TWF can now normally make 2 attacks per Attack action (thanks to Extra Attack), plus the 1 bonus-action attack. Dread Ambusher lets them make 4 attacks on the first turn (3 attacks during their Attack action, 1 attack as a bonus-action from TWF), and 3 attacks per turn for the rest of the fight.

Answer 2

The rule for Dread Ambusher states that it is part of the one Attack action, and only in your first turn (emphasis mine):

At the start of your first turn of each combat, you 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 that weapon's damage type.

This means that you roll to hit twice. If the second attack hits, you add an additional d8 damage to that attack. So yes, if you target one creature, and they die in the first hit, the second attack is effectively wasted, unless there is another creature within reach (i.e. 5ft, or 10ft if you have a melee weapon with reach). You can also move between attacks provided you have the movement left to do so.

However, this is not restricted to melee weapons only. Meaning that if you make a Ranged weapon attack with a bow for example, you can shoot the first target, they die, then shoot another target.