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Here’s the basic rule for Surprise (Player’s Basic Rules, p. 69):

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 counter.

I’m not sure how to interpret that last sentence.

For example, suppose that the players try to sneak up on on some monsters, so they roll Dexterity (Stealth) checks. The thief and the champion both roll 14, but the evoker only rolls 9. The DM compares this to the monsters’ passive Perception: a cyclops with 8, a dire wolf with 13, and a giant owl with 15.

The cyclops doesn’t notice any threat, so it’s surprised. The owl notices all the threats, so it’s not surprised. But what about the dire wolf? It notices the evoker but not the rogue or the champion. Which is correct:

  • The dire wolf noticed a threat (the evoker) so it’s not surprised.
  • It didn’t notice a threat (the rogue and champion) so it’s surprised.

If the former is true, could the rogue and champion take advantage of the group check rule to help the less-stealthy evoker hide from the dire wolf? Group Checks (Player’s Basic Rules, p. 59):

To make a group ability check, everyone in the group makes the ability check. If at least half the group succeeds, the whole group succeeds. Otherwise, the group fails.

Group checks don’t come up very often, and they’re most useful when all the characters succeed or fail as a group.

An earlier question covers a couple of related situations, where a rogue sneaks up separately from the rest of the players, or where all of the monsters use a single group Dexterity (Stealth) roll, but not this case where all of the players try to sneak with different rolls.

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2 Answers 2

There are two ways to interpret that sentence, and it hinges on a weirdness of how English uses the indefinite article.

Any character or monster that doesn’t notice a threat is surprised at the start of the counter.

The usual interpretation of "a threat" here is that it means "one threat". If that is the correct reading, your question is the result. Is it correct though? This meaning would require that surprise is a relationship between two individuals, so that the dire wolf could be surprised by the rogue but also not surprised by the enchanter.

Is this how surprise works? It turns out, no:

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. (PBRv0.2, p. 69)

Surprise is not a relationship between two entities, it is a state of a single entity. It's impossible to be surprised by one opponent but not surprised by another.

Is there another way to read that sentence about "a threat" that makes surprise sensible as a state? As it turns out, yes.

"English is funny that way"

Another use for the indefinite article, which looks identical to the "one threat" meaning, makes the sentence in question

Any character or monster that doesn’t notice a threat is surprised at the start of the counter.

mean any threat at all, not just one. If this meaning of "a threat" is how it's being used, then that means only creatures who notice no threat are surprised.

Because this reading is perfectly normal English, but ambiguous, we need to confirm the reason by looking for clues in the surrounding text. That confirmation is in the definition of surprise we looked at above: being surprised means being completely surprised, which only makes sense if it happens when no threat is noticed.

So the dire wolf is not surprised, because it did notice a threat, as opposed to not noticing a threat. (See how that makes sense put that way?)

On the plus side, the champion and the rogue don't need surprise to have advantage on the dire wolf, because that doesn't rely on surprise, but rather on being unseen, and being unseen is a directional relationship, not a state.

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Yes, unfortunately sentences like this are ambiguous in English – the not is an even bigger problem than the indefinite article – but I like the approach you took to resolving it. I was thinking along the same lines myself, that surprise makes more sense if you interpret it that way. –  Bradd Szonye Aug 20 at 0:55

RAW: Your first bulletpoint is correct, the 2nd is wrong.

There are two ways to play this, the first is RAW as I understand it and the second is a houserule which I believe supports the spirit of the rules.

Option 1, RAW: If a creature can detect any enemies it is not surprised

As the surprised section states:

Any character or monster that doesn’t notice a threat is surprised at the start of the encounter.

I can see where the confusion might come it, you are possibly interpreting "a" as meaning a specific threat, whereas I believe "a" is used in this case to mean "any" threat. Even if they can't see the Rogue or the fighter, they noticed other guy and are on guard for attacks. As such they are not surprised.

Option 2, Houserule: Treat all stealth rolls as partywide checks.

The DM decides who might be surprised.

This simple sentence preceding the explanation of comparing passive perception vs. stealth checks leads me to believe that DM Fiat is supported in this case. As such I suggest partywide stealth checks.

If the majority of the party would beat the passive perception of the monster's passive perception then the party would get a surprised round against said monster. For this to work though it needs to cut both ways and monster stealth checks should equally work if they beat the majority of the party's passive perceptions.

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@BraddSzonye edited intro to reflect that option 1 is RAW and option 2 is a minor houserule –  Joshua Aslan Smith Aug 20 at 0:46
    
Thanks, I think that’s an improvement, although I still don’t think the group passive Perception is a good idea. (The rest of the house rule is good, though.) –  Bradd Szonye Aug 20 at 0:48

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