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As a DM, I'm wondering if allowing a group to use social skills instead of stealth in some situations would still be within the rules or fall under the house rules category.

I have in mind a group of characters in disguise, approaching an outpost and talking their way in before suddently attacking. Could a successful Charisma (deception) check vs the creatures' passive Wisdom (insight) cause their enemies to be surprised?

While the wording of surprise seems rather narrow, constraining it to a stealth check, I'm leaning on the following phrase to broaden the possibilities :

"Any character or monster that doesn't notice a threat is surprised at the start of the encounter (PHB, p. 189)"

It seems to me that "noticing a threat" could mean much more than "not actually be aware of the presence of someone".

In the end, I know it'll come down to a table-specific decision (as, per the spirit of this edition, most rulings should be), but we're still learning the 5e rules and trying to follow them as strictly as possible (so we can feel how things are balanced) before houseruling anything.

So, houserule or DM's fiat?

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  • \$\begingroup\$ You might also consider as modifiers factors such as how well the characters doing the "talking their way in" are able to mimic local mannerisms/accent/dialect/fashions/shibboleths to put the enemy at ease. If there's something in that character's backstory having known someone from the target well enough to pick up the patois, give him a +1 or +2 for that. ("My aunt was a slave in $Enemytown before she was able to escape; and she taught me how to fit in there.") \$\endgroup\$ – Monty Harder Apr 27 '16 at 19:41
  • \$\begingroup\$ Sure. As would do spells like Disguise self or Polymorph. \$\endgroup\$ – Meta4ic Apr 28 '16 at 10:32
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Short answer: yes, your citation from the PHB supports character initiative or action as the trigger from non-combat to combat.

It's not necessarily "another skill" that can set up surprise, but player actions, preparation, and decision.

Surprising Foes. If the adventurers encounter a hostile creature or group, the DM determines whether the adventurers or their foes might be surprised when combat erupts. (p. 65, Basic Rules)
Any character or monster that doesn’t notice a threat is surprised at the start of the encounter. (p. 69 Basic Rules)

While the second point is under the "Combat" rules, the surprised condition means that for some or all members of one side, combat actions start later than the other side since actions based on surprise (or lack thereof) are taken into account before any initiative order turn based actions and reactions play out: it complicates the implementation of "roll for initiative!"

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.

Two points worth noting:

  • Surprise can be determined to affect a whole side, or individuals.

  • From a rules perspective, surprise is explicitly linked to combat in terms of its significance, which is addressed in detail here.

  • If a party is surprised, but no combat ensues, a lot of the detailed treatment of surprise is rendered irrelevant.

Discussion

Don't let the rules be an obstacle to play

In an attempt to "follow the rules as strictly as possible" in the perspective of "Rules as Written" it is well to also embrace the two other manifestations of the rules in this edition's design as expressed by Jeremy Crawford here.

RAI ... “rules as intended.” This approach is all about what the designers meant when they wrote something. In a perfect world, RAW and RAI align perfectly, but sometimes the words on the page don’t succeed at communicating the designers’ intent. Or perhaps the words succeed with one group of players but fail with another. When I write about the RAI interpretation of a rule, I’ll be pulling back the curtain and letting you know what the D&D team meant when we wrote a certain rule.

RAF. Regardless of what’s on the page or what the de-signers intended, D&D is meant to be fun, and the DM is the ringmaster at each game table. The best DMs shape the game on the fly to bring the most delight to his or her players. Such DMs aim for RAF, “rules as fun.”

The transition isn't all about "roll for initiative!"

The transition from non-combat to combat in an encounter is based on a trigger, an action, or a decision. Your question gets at the heart of that transition, which is often something other than the DM saying "roll for initiative." By setting up the trigger condition, and letting it develop that way, the DM empowers players and ensures their agency (if they do a good job of setting it up and describing the set up/plan, etc). This gets at the fundamental structure of play.

How the game is played:

(Basic Rules, Page 3)

  1. The DM describes the environment
  2. The players describe what they want to do.
  3. The DM narrates the results

Note on point 3: the DM determines results (like whether surprise happens or not), which includes taking into account what effort the players are exerting to set up that condition.

When there is a chance for failure, or when success or failure is an interesting outcome (such as "did we achieve surprise or not?" in your scenario) then any die roll is based on DM Judgment. That is also what the rules spell out. The DM's role includes the requirement to make rulings. The rules in D&D 5th edition are not computer code. They are not a string of on/off switches. They include judgment, which is a human aspect, and which opens the door for a DM to determine "you make that attack with advantage because ..." or "you make that check with disadvantage because ..." and so on.

About terms:

  • DM Fiat far too frequently attracts a pejorative connotation, which is unfortunate. DM judgment, (and a DM choosing not to metagame but instead role-play the NPCs/Monsters) is what makes or breaks a game.

  • It isn't a house rule for a DM to act like a DM.

    Then the DM determines the results of the adventurers’ actions and narrates what they experience. Because the DM can improvise to react to anything the players attempt, D&D is infinitely flexible, and each adventure can be exciting and unexpected. (p. 2, Basic Rules)

DM judgment is part of the rules. (The infamous rule zero). If a DM doesn't apply judgment, then that role isn't being fulfilled.

Can we do this?

Absolutely, yes. The players characters attempting to lull the NPC's into not expecting an attack, and then suddenly attacking, is the essence of a surprise attack or an ambush, and is their input to the game flow (step 2) once the DM's description of the setting (set 1) is fulfilled.

Which opposed ability checks, if any, are necessary are a function of steps one and two: the DM describes the environment, and the players describe what they are attempting.

If successful, they'll surprise the guards. If not, oops, the jig is up!

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    \$\begingroup\$ I agree with this answer in general except that it conflates surprising someone with acting before them. The combat rules call for initiative after surprise has been determined: if the surprised creature rolls well on initiative their turn comes first and they are no longer surprised when the surpriser acts. \$\endgroup\$ – Dale M Apr 28 '16 at 5:25
  • \$\begingroup\$ @DaleM You're right : higher initiative gives the target a chance to use it's reaction and is no longer surprised when it's hit (it matters when you face an Assassin!). But this is another question (for which you helped assembling extensive answer here : rpg.stackexchange.com/q/65461/26074. In my opinion, if we replace "for one side, combat starts later", in the 4th paragraph, with "for some enemies, combat starts later", that would pretty be it for the conflation. \$\endgroup\$ – Meta4ic Apr 28 '16 at 10:21
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    \$\begingroup\$ @Meta4ic I used "for some or all members of one side, combat starts later", because how initiative is determined can make that vary. \$\endgroup\$ – KorvinStarmast Apr 28 '16 at 12:38
  • \$\begingroup\$ @DaleM I added a link to your treatment, and modified the description, but really want to keep this answer narrow in scope. (it's too long as it is, probably needs some trimming) . \$\endgroup\$ – KorvinStarmast Apr 28 '16 at 12:40
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Strictly RAW, Surprise is related only to being stealthy:

Surprise (PHB p. 189)

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.

That being said, from a RAI perspective, the situation you describe aligns perfectly with the intent of preparing a surprise attack, and it would be fun - which is (or should be) one of the reasons you're gathering around a table and rolling oddly shaped dice.

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Characters can surprise others using a Dexterity (Sleight of Hand) check in some cases. For instance, one character may pull out a dagger and stab someone who they were just previously having a friendly conversation with. I'm not sure if that can be found in the PHB, but it makes sense. In the same vein, it's plausible that a successful Charisma (Deception) contest could cause an enemy to let their guard down, leaving them vulnerable to a surprise attack.

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  • \$\begingroup\$ Welcome to RPG.SE. Please take the tour and have a look around the help center to see how this site works, and how it compares to the other SE sites where you participate. Happy Gaming! \$\endgroup\$ – KorvinStarmast Apr 28 '16 at 0:40
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Many "surprising" things occur in a dungeon filled with deadly traps and vicious monsters, but not all of them constitute Surprise, causing the loss of one's first turn. The rules rest the ultimate decision of who's surprised soundly in the discretion of the DM. See PHB pages 183 and 189.

I've been in several table arguments about whether a creature should have to roll vs. Surprise against another creature that it's aware of when it's utilizing disguises, hidden weapons, sudden betrayals, or ambushes during certain... vulnerable moments. As DM, if you feel that Surprise is too powerful, you could instead give advantage or disadvantage to Initiative. Just make sure you're not being vindictive against players because they outwitted your prized encounter with a clever disguise or pulled a switchblade on your favorite NPC.

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  • \$\begingroup\$ True. As for your last part, it's actually quite the opposite : I'm trying to find ways to push them towards more creative dealings with encounters. \$\endgroup\$ – Meta4ic Apr 28 '16 at 10:00

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