The surprise round and you

[zaratan]

No. If only one passes, then 9 have failed ". . . to catch you unawares." The quote says "that if even one . . . fails to catch you unawares" then you are not surprised.

sorry, only read now.
So, if 9 enemies suceed and only 1 fail, no surprise round? Man, ambush in group is a terrible idea.

 

[MechaPilot]

sorry, only read now.
So, if 9 enemies succeed and only 1 fails, no surprise round? Man, ambush in group is a terrible idea.

If the group doing the ambushing is not good at stealth, I totally agree. I think that's also the point of it though. That prevents a party of noisy, heavily armored PCs/foes from sneaking up on someone because they have one or two high-Dex, lightly armored allies sneaking with them.

 

[Ristamar]

sorry, only read now.
So, if 9 enemies suceed and only 1 fail, no surprise round? Man, ambush in group is a terrible idea.

It's not so bad if the DM allows Group Stealth checks and the ambushing party has a few very competent individuals. Well, I guess it would still be bad if you're on the receiving end of it...

 

[Flamestrike]

sorry, only read now.
So, if 9 enemies suceed and only 1 fail, no surprise round? Man, ambush in group is a terrible idea.

Repeat after me: There is no such thing as a surprise round.

During the first round of combat, when it gets to a creatures turn if that creature is aware of even just the single enemy creature, it is not surprised and can act normally. If it is unaware of all enemy creatures, it is surprised and cannot take any actions or move on its turn (its surprised).

So in your example, each PC is aware of at least one creature on their first turn and are not surprised (and can act normally).

That said, PCs 2 and 3 are not aware of at least one creature each on turn 1. They cannot attack those creatures (theyre hidden) - they can only attack the ones they noticed (via perception). Once those hidden creatures act, they do so using the 'hidden creature' rules - i.e. they attack with advantage.

Just because your buddy flubbed his stealth check result, while this may alert your foes to the presence of danger and ruin the element of surprise, it doesnt reveal your presence or make you no longer hidden.

 

[spectacle]

sorry, only read now.
So, if 9 enemies suceed and only 1 fail, no surprise round? Man, ambush in group is a terrible idea.

If you have time to prepare then you can have each ambusher repeat the hide action until they roll well and hide properly, and you can have some characters using the help action to give advantage on the stealth check for others. Then you just need to wait for the targets to show up and hope that none of them have super high passive perception.

This way even a stealth-challenged groups can set up an ambush, given enough time to prepare. Trying to sneak up on someone with a large noisy group is pretty sure to fail though, and that is how it should be.

 

[Azurewraith]

If you have time to prepare then you can have each ambusher repeat the hide action

Why even roll if your just going to keep repeating it? Just pull a number out yhr ether. Tad to Meta gamey for my taste aswell.

 

[DEFCON 1]

I've modified at my table to try and merge these two opinions (well, to end stupidity and to keep close to the rules):

Everyone rolls initiative just as the OP describes, But the "Triggering" creature/event/whatever goes first at their initiative. So in the OP's scenario, round 1 BEGINS at initiative count 6. The enemies are surprised and have not acted yet in the round. At the top of round 2, the guards end their surprise (well, technically end surprise...a bolt stuck in the arse is damn surprising!) and the Assassin goes again.

Yep, that's one way of doing it. In my games, in the case of everyone on one side being successfully Hidden (whether it's one single person, a couple people, or the entire party), I just let whomever is going to start the combat go first in the initiative order without having to roll, because I don't roll initiative until after the "triggering" event has completed. So the person starting combat goes first and everyone else rolls initiative and goes in order after that... some participants probably being Surprised and thus not being allowed to act when their initiative count comes up in that first round.

I personally don't go along with the Sage Advice ruling that a target can react to a trigger before the trigger has happened, because I find it too silly based on how often that will actually occur. Sure, an unaware creature could maybe react to a bow firing from out of nowhere and somehow dodge it to not take the massive damage it would cause once in a blue moon... but I just don't believe it would happen with the frequency it would due to how D&D initiative works. The way D&D initiative is set up and the ease at which a target can roll high and then go first, you'd probably see every third combat have a target with the reaction sense of Daredevil. Which I just choose not to go along with.