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

advantage-and-disadvantageattackdnd-5eranged-attackstealth

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.

Best Answer

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.