Stealth and surprise confuse me

[tchntm43]

The rules on this subject (PH 189) seem to only make sense if everyone one each side rolls the same stealth check. Or if only parties of 1 are being stealthy. What I don't understand is what happens when some members of one side are surprised by only some members on the other side. Here's an example to better illustrate my confusion:

Party
Character 1. Stealth check: 15, Passive Perception: 11
Character 2. Stealth check: 8, Passive Perception: 13
Character 3. Stealth check: 18, Passive Perception: 9
Character 4. Stealth check: 11, Passive Perception: 11

Bad guys
Orc: Stealth check: 8, Passive Perception: 10
Bugbear: Stealth check: 19, Passive Perception: 10
Mindflayer: Stealth check: 11, Passive Perception: 16

According to the rules, it sounds like:
Character 1 is surprised by the bugbear, but notices the mindflayer and orc.
Character 2 is surprised by the bugbear, but notices the mindflayer and orc.
Character 3 is surprised by the bugbear and the mindflayer, but notices the orc.
Character 4 is surprised by the bugbear, but notices the mindflayer and orc.
The orc is surprised by Characters 1, 3, and 4, but notices character 2.
The bugbear is surprised by Characters 1, 3, and 4, but notices character 2.
The mindflayer surprised by Character 3, but notices Characters 1, 2, and 4.

Which ones skip their first turn?

[Scarytincan]

I feel like an example could have been given with far fewer pieces to keep track of.

Who notices whom first and what do they choose to do when they see the enemy?

[Rebonack]

There are rules for group Stealth checks. If half or more of the group passes the target DC, then they don't get noticed. If half or more fail, they all get noticed.

In this case we have two competing group Stealth checks. Half or more of the players are beating the bugbear and orc, so the bugbear and orc are both Surprised. The mind flayer is not.

Of the players, only Player 3 is failing to beat the enemy group Stealth check, so only Player 3 is surprised.

[stoutstien]

There are rules for group Stealth checks. If half or more of the group passes the target DC, then they don't get noticed. If half or more fail, they all get noticed.

In this case we have two competing group Stealth checks. Half or more of the players are beating the bugbear and orc, so the bugbear and orc are both Surprised. The mind flayer is not.

Of the players, only Player 2 is failing to beat the enemy group Stealth check, so only Player 2 is surprised.

2nd this.
I immediately use group chats if there's more than three possible combos.

Also the surprised condition doesn't skip your turn. It just prevents any action bonus actions reactions from being used. Most of the time it doesn't make a difference but there are some cases where the distinction is important. The assassin rogue comes to mind

[Erys]

In your example no one is surprised.

Also, no one skips their first turn. 5th ed does not do surprise rounds like previous editions.

Let me explain:

The DM determines who might be surprised. If neither side tries to be stealthy, they automatically notice each other. Otherwise, the DM compares the Dexterity (Stealth) checks of anyone hiding with the passive Wisdom (Perception) score of each creature on the opposing side. Any character or monster that doesn’t notice a threat is surprised at the start of the encounter.
If you’re surprised, you can’t move or take an action on your first turn of the combat, and you can’t take a reaction until that turn ends. A member of a group can be surprised even if the other members aren’t.

So, if anyone on either side of your example notices even one person from the other side, they should not be surprised. Anyone who completely bombs their perception would be surprise.

The thing to remember is: surprised or not you roll initiative as usual. The reason being when you get your turn you have access to reactions once its over. If you are surprised but also have a high iniative you could still use a reaction to say, cast Absorb Elements when the enemy casts a Fireball on their turn later in the round.

[Vorpalchicken]

No one would be surprised under these conditions. With group stealth checks, things might change. There you would look at the best two stealth rolls only.
Or if the stealthy guy separates from the non stealthy guys (the rogue scouts ahead) but that's dangerous. Mr stealthy would have to be well ahead of the rest of the party (say 90 feet in a dungeon.) He might get surprise easily but on round two he could be in trouble.

[Tanarii]

IMO the surprise rules are designed for ambushes, so usually two groups aren't trying to ambush each other. It's one side or the other, having previously detected the other side, and attempting an ambush. Often with non-stealthy types far enough behind that stealthy types have a chance (PCs or particularly ambush-y monster types), or - solo stealthy monster stalking the party.

The surprise rules could be used for two groups sneaking along and bumping into each other, especially in a short range environment (like a dungeon) or in a particularly hostile area (scouts in a war zone). But unless you've got two particularly stealthy groups, that's usually going to result in either the stealthy scouts far enough ahead of the main body being the only ones involved, or no surprise on either side.

Also group stealth checks explicitly go against the basic surprise mechanic laid out. Each creature checks individually. The surprise rules can either be read as 'DM-fiat or use X mechanic' or 'generic statement about DM determining surprise, and here's X mechanic DM uses to do determine it'. In the former, the DM can of course fiat group checks if they prefer. In the latter, they're house-ruling a change.

[Vorpalchicken]

Also group stealth checks explicitly go against the basic surprise mechanic laid out.

Does it actually explicitly say this somewhere in one of the books? It seems like it would work to me. The passive perception that each potentially surprised individual would have to beat would be the lower of the two highest (if there are three or four in the party) stealth rolls.

In other words, the stealth check is a group check (in the OP example using the top two rolls) opposed by individual passive perceptions.

So using group stealth in the OP example (assuming both sides were trying to be stealthy), the Orc and the Bugbear would be surprised (PP was lower than 15) and character 3 would be surprised. (PP was lower than 11) The Mind Flayer and Characters 1, 2 and 4 would act in the first round.

[Tanarii]

Does it actually explicitly say this somewhere in one of the books?

Yes.

DM compares the Dexterity (Stealth) checks of anyone hiding with the passive Wisdom (Perception) score of each creature on the opposing side. Any character or monster that doesn’t notice a threat is surprised at the start of the encounter.

Each stealther makes their own check opposed by all opposing creatures.

This, as I said, is the mechanic presented. There's a preceding sentence that the DM determines who might be surprised. You can read that as introductory (ie they do it using the mechanic). Or a general rule, of which the mechanic is one subset or method of resolution. In which case a group check would be a (apparently somewhat commonly used) DM option alternative.