D&D 5E Can a Critical Hit miss?

Scenario: Party is proceeding down a wooded path at night with torches. Heavy foliage lines the path, which is 30 feet wide. Noise off the side of the path up ahead draws their attention. PC#1 goes up to check it out, is asked to roll Perception and fails. Crossbow bolts are fired out of the dark, heavy foliage and strike PC#1. PC#2 asks if she saw the spot from where the bolts were shot. DM asks for Perception roll and there is a success. PC#2 fires her bow into that exact spot, rolling a natural 20. Unbeknownst to anyone in the party, after firing the crossbow bolts, the two enemies were able to stealth away from that spot (rolled higher on Stealth than any of the party member's Passive Perception).

How do you, as DM, rule that Crit?

Assumptions
Raiders are heavily obscured (on the edge of it) and the Travellers are lightly obscured.
Raiders are hidden at the start.
Raiders get superior initiative on the travellers as the travellers work their way towards them (technically this means they also won init over all the travellers.) Surprise is not indicated and also not necessary for the example.
Turn 1 -
Radier 1 fires from hidden, reveals his position to the approaching target but is still heavily obscured. radier-1 then uses a bonus action hide ability (perhaps a rogue?) to also hide and move away quietly. (Stealth vs perception determines if he manages to hide - if not - his position is still known.)
Raider-2 does the same.
Traveller-1 (pincushion) At this point, no perception check is needed to know where they fired from. If any of the stealth checks were failed, the position of those who failed even after movement is also known - no check required. Either way, they do not know (and know they don't know) the location of the raiders who succeeded at the stealth. Pincushion can choose to fire on the old spot but does so knowing they may or may not be there. Either way, pincushion fires with disadvantage because they are shooting into an area with heavy obscurement and thus - blinded - unseen rules apply - not to see if they hit the spot but to see if they hit anything of import in that spot. if they fire into an empty spot - the final result will be a miss. if they fire into an occupied spot and score a crit (double 20's) its a hit and a crit.

The big key takeaways are:
You need some special feature to let you shoot and then hide - usually they require bonus actions.
In this case, the "unseen" comes from the area the raider is in, not the stealth, so even while they attack, the attacker remains "unseen" but their location is revealed "no longer hidden.". (Would be different if they were unseen by dint of the "hide action" say in light foliage. Would be different if the raiders could not see thru whatever is heavy obscuring them.)
The default is you can perceive the location "not hidden* and if you hide then the other guy should know they can no longer hear where you are... that **should** be made clear to the player by the GM.

AFAICT:

1. It would take Rogues or Goblins etc with bonus action Hide to be able to pull off the attack - hide - move combination.

2. Players can declare they're shooting at the area an attack came from even if they can't see anyone there.

3. Player attack will have disadvantage as unseen target.

4. So a crit would require a double '20'.

I guess in that circumstance - goblin ambush then double-20 - I'd declare the PC's bolt had impaled a passing squirrel.

The attackers could have used cunning action to get away, and in any case, there is no indication in the description about how long the group took to react etc.

It doesn't matter if someone rolls a 20 to hit a square where no-one is standing. It hits no-one.

When firing into darkness or god or anything else which gives total concealment and is more than a 5ft square you have to nominate a target spot (a 5ft square). If there is no target there, you cannot, no matter what you roll, hit the target.

The fact they made a noise did NOT reveal their precise location as per RAW, so once again is irrelevant to whether the shot hit.

ad_hoc said:

Is it fun to roll a 20 and miss?

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Is it fun to have encounters with hidden opponents? Sometimes, I wouldn't overdo it.

Firebolt hits it just doesn't do damage. That is different.

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It seems about the same to me, but no biggie. Curious though, would you have the player roll damage here? (IE, they critted with firebolt against an opponent immune to fire.)

DM Dave1 said:

Scenario: Party is proceeding down a wooded path at night with torches. Heavy foliage lines the path, which is 30 feet wide. Noise off the side of the path up ahead draws their attention. PC#1 goes up to check it out, is asked to roll Perception and fails. Crossbow bolts are fired out of the dark, heavy foliage and strike PC#1.

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So far so good. PC#1 should have gotten a passive perception to notice the location of the attackers, and possibly an active perception on top of that. Remember that since PC#1 didn't see the attackers they have advantage on their attack.

DM Dave1 said:

PC#2 asks if she saw the spot from where the bolts were shot. DM asks for Perception roll and there is a success.

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If someone attacks, you know where they are attacking from, no check needed. There are some special feats that override this.

Page 73 Basic Rules

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

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However, all they know is where the attack came from. While normally hiding takes an action, if the attackers can hide as a bonus action after the attack they are free to do so at no penalty.

DM Dave1 said:

PC#2 fires her bow into that exact spot, rolling a natural 20. Unbeknownst to anyone in the party, after firing the crossbow bolts, the two enemies were able to stealth away from that spot (rolled higher on Stealth than any of the party member's Passive Perception).

How do you, as DM, rule that Crit?

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If you are attacking a target you cannot detect, you are guessing their location. In this case, PC #2 guessed the wrong location. I probably would have let them know they weren't certain the attackers were still there, but other than that I think you ruled correctly. PC#2 targetted an unoccupied square, not a legitimate target so the attack misses. They attacked the darkness.

On subsequent rounds, PCs can ready to attack the moment they are attacked. This is sometimes the best strategy, especially against creatures that can hide easily.

S'mon said:

....

I guess in that circumstance -....ambush then double-20 - I'd declare the PC's bolt had impaled a passing squirrel.

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Suddenly an angry Moose charges the party yelling "you killed Rocky!" After overdrawing your pcs Visa and MasterCard it wanders away looking for a Mountie.

Along with the very good advice above, I would add that after the balloon goes up, an attempt to stealth away wouldn’t be contested by passive perception, as the PCs would be on high alert after one of their party has been taken out. So it would be contested Stealth vs Perception rolls IMHO.

jasper said:

Suddenly an angry Moose charges the party yelling "you killed Rocky!" After overdrawing your pcs Visa and MasterCard it wanders away looking for a Mountie.

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As long as it was just a squirrel and not a miniature giant space hamster everything should be fine.

Mistwell said:

You are no longer hidden if you attack someone even if the attack misses (unless you have the Skulker feat).

{snip}

At least, that's the rules. I'd argue they are wise ones. As soon as you start letting creatures attack and auto-hide due to existing cover and make them immune to being perceived, players will start massively abusing that when they can. It's not a particularly good path to go down, in my opinion. It's pretty clean and simple that when you attack you're no longer hidden.

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These are great points. At the very least, there needs to be a contested skill check for the Move and Hide after the crossbow shots (as [MENTION=6801558]robus[/MENTION] mentions above).

ClaytonCross said:

Example 2: "what was the players intent and how would the players character approach that task"

{snip}

Player said do I see where the arrow came from not do I see who shot it.

I think its bad GMing but people have different styles.

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Agreed. The DM in the situation was too nitpicky with PC#2's Perception check. Succeeding on Perception should have given away the crossbowfolks' position, too.

All of that said, if I were this DM and bungled the various rulings up to the point where PC#2 shot, I hope I would have had the sense in the moment to rule as follows on the Crit:

"Your arrow flies through the thick foliage. You hear your arrow ricochet off of something hard and then you hear an audible yelp about 10 feet away from the spot. Roll your crit damage."

That would be much more satisfying to the table than just saying "Sorry, even though you rolled a 20, you missed" in this situation - especially with the lack of solid RAW/RAI justification for everything leading up to that point.

robus said:

Along with the very good advice above, I would add that after the balloon goes up, an attempt to stealth away wouldn’t be contested by passive perception, as the PCs would be on high alert after one of their party has been taken out. So it would be contested Stealth vs Perception rolls IMHO.

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DM Dave1 said:

These are great points. At the very least, there needs to be a contested skill check for the Move and Hide after the crossbow shots (as @robus mentions above).

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Technically, in combat, it would be the NPC or monster's Dexterity (Stealth) against the PCs' passive Perception. If the NPC or monster was determined to be hidden, the PC could opt to take the Search action in which case it would be a Wisdom (Perception) check versus the monster's Dexterity (Stealth) check result as an action. The PCs' passive Perception check would be the floor.

It sounds like these PCs were undertaking the Search action for free. But it's also not clear whether the NPCs or monsters were actually hidden.