When using a Longbow from hiding with Extra Attack, can I nock 2 arrows and fire them at once to attack twice with advantage?

Question

Today I was searching for some 5th edition rules to clarify attacking with a longbow from stealth and how the fighter's extra attack feature interacts with gaining advantage from attacking from stealth.

I was able to confirm from a Sage Advice response that only the first attack from stealth is considered a surprise attack from stealth, and only that first attack gains advantage. Attacks after that do not gain advantage.

How would that interact with an archer that nocks 2 arrows in the bowstring to fire 2 arrows with one "attack" of the longbow? Would both arrows gain the advantage of being fired from stealth? or just the first one that lands on a target?

This might just be my way of flavoring up the RP of having the extra attack feature as an archer, but I wanted to be sure of the technical aspects of the attack before I do it at our table and cause a rule confusion.

My Google-fu didn't bear much for results, so I'm hoping some can steer me in the right direction here.

Answer 1

Strictly by the book, only your first attack has advantage

A longbow has the ammunition property. The ammunition property states (emphasis mine):

You can use a weapon that has the ammunition property to make a ranged attack only if you have ammunition to fire from the weapon. Each time you attack with the weapon, you expend one piece of ammunition...

As far as the rules are concerned, you can't mechanically fire two arrows at the same time; you have to fire one arrow and then the other. From there we know that you lose any benefits from being hidden when the first attack hits or misses, as mentioned in Baergren's answer:

If you are hidden—both unseen and unheard—when you make an attack, you give away your location when the attack hits or misses. (PHB p.195)

So unless you had managed to hide again between shots, or had some effect like the Skulker feat, which allows you to remain hidden if you miss a shot from cover, only the first attack will have advantage.

Of course, the DM can rule otherwise

Your DM can make whatever ruling they feel is reasonable about whatever you are trying to propose. I have never come across this situation in my own games, so I will refrain from proposing any solutions, as they would all be untested. Just know that in this case, your DM is going to have to make a call. Whatever the DM rules at that point is what you're going to have to go with.

Answer 2

You can't fire two or more arrows at once

Despite being a common fantasy trope, shooting a bow with multiple arrows simultaneously is impossible, both in reality and in 5e. The Extra attack feature allows you to shoot faster, effectively making two or more attacks during the 6-seconds round. But they are still separate attacks - all can be launched into different foes, and each needs its own attack roll.

Answer 3

Nocking 2 arrows is an improvised move. Totally up to the DM what happens. I would rule as follows: You're hidden, you gain advantage. You're improvising a difficult shot, you gain disadvantage. Netting you make 2 to-hit rolls as normal.

So your best gain would be to take the first shot at advantage.

Answer 4

When a creature can't see you you have advantage on attack rolls against it. (PHB p.195)

Emphasis mine. This states rolls (multiple) so yes, all attacks made by you against a creature you are hidden from have advantage. I imagine it would say first if it were restricted as such.

However it could be argued that you are seen after the first attack hits.

If you are hidden—both unseen and unheard—when you make an attack, you give away your location when the attack hits or misses. (PHB p.195)

This might be a DM call if your attacks are in quick enough succession to be considered functionally simultaneous, which I would argue they would be.

Answer 5

5 arrows is maybe a stretch but reasonably draw up to 3 arrows at the same time since you have 3 places between your fingers that can hold arrows in a drawing position

Though, yes, the accuracy decreases a slight amount for each extra arrow you have but the middle arrow tends to lose the least accuracy.

Depending on how many arrows you draw, the shot also changes if you're drawing 2; the arrows tend to fly straighter but if you draw 3 arrows the top and bottom arrows tend to split off to the sides and the middle stays relatively true to its starting position.

Anything more then 3 arrows and i don't see how you could logically hold them.

You also have to account for the bow's Orientation: is the person trying to draw on a Horizontal or Vertical, a Horizontal draw would give the arrows more stability but you would have to sacrifice Aim-Down-Sights for hip fire.