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I recently ran an encounter on a "restaurant boat" where my players had to obtain info from a noble on board. They successfully bluffed/bribed/sneaked their way on board. Certain areas of the ship were off limits to guest, such as the crew's quarter's, the captain's cabin, and the lower deck with rowers moving the ship along.

My players found a somewhat quiet spot on deck. They proclaimed they wanted to sneak past the guests, who were busy with eating/socializing/etc., into the forbidden areas. One of them cast pass without trace, and I asked them to all roll for Stealth. No one got less than 19 on their Stealth check (after modifiers). They then proceeded to "sneak" past guests into the upper areas (not forbidden per se) and then further into "Staff Only" areas.

How do I adjudicate this?

Obviously, they pose as guests, no weapons or armor on, so they would just blend into the crowd and then, in an opportune moment, sneak past a door/curtain/rope barrier. But they are still moving in plain sight of at least a dozen NPCs. The NPCs can probably see them, but they do not perceive them.

The same problem would arise for me if they wanted to escape someone following them in a dense marketplace or in a crowded tavern. How can you Hide/roll for Stealth in a crowd of - admittedly uninterested in you - NPCs?

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Stealth was most likely the wrong choice

Stealth implies that you are impossible to see. If you succeed on your stealth attempt, you are hidden, if you fail, you are not hidden.

Your players aren't actually trying to be hidden, anybody can see them, they simply don't register them as somebody who shouldn't be there.

Blending in with the crowd really shouldn't require a stealth check at all. It might, however, if you like, entail any of the following:

  • Persuasion: To get other guests to cooperate if they at some point figure out things are fishy.
  • Deception: To bluff their way past guards who are suspicious about the players actually being guests
  • Performance: Deception works great for pretending to be a guest when you are not, but performance could also work, depending on who you ask.

None of these things require stealth, because you aren't trying to be unseen, you're trying to blend in.

Stealth doesn't enter the ordeal until they actually try to go somewhere a normal guest would not be allowed. The moment they want to pass into Staff Only areas and the guards would react if a normal guest did that, then they have to actually use their stealth skill, and they would obviously have to do so in a way that makes sense, you can't stealth your way through a door in plain sight, regardless of how well you rolled.

Blending into a crowd to escape from somebody else is a completely different thing than blending into a crowd to not stand out. Once your target no longer has line of sight to you, you can try to stealth. If you succeed, the target no longer knows where you are and you can keep moving in the crowd until they have direct line of sight of you again, at which point you are no longer hidden and the chase most likely continues.

It's the difference between: "I need to hide in the crowd because I'm a wanted man and if I'm spotted they will arrest me!" and "I need to blend in because I don't want to look out of place and get asked questions by nosy guards."

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    \$\begingroup\$ The "you aren't trying to be unseen, you're trying to blend in" bit should be at the top in bold as the tl;dr. That's brilliantly succinct and accurate. \$\endgroup\$ – GcL May 29 at 14:05
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    \$\begingroup\$ @GcL, agreed. There is a big difference between "not being seen" and "not being noticed". I forget which book, but one of the Hitchhiker Guide books talk about the "SEP" field for cloaking. It doesn't turn the object invisible, in fact, it does quite the opposite. "The Somebody Else's Problem field... relies on people's natural predisposition not to see anything they don't want to, weren't expecting, or can't explain." \$\endgroup\$ – MivaScott May 29 at 17:37
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    \$\begingroup\$ @MivaScott -- one of the most effective tactics for not being noticed as out of place in today's world is to wear a hivis vest and hardhat -- that way, you're presumed to be construction/maintenance and thus allowed to go wherevs :P \$\endgroup\$ – Shalvenay May 30 at 2:47
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    \$\begingroup\$ "'Stealth implies that you are impossible to see." "Your players aren't actually trying to be hidden" "None of these things require stealth, because you aren't trying to be unseen" - I think you are confusing Stealth with Hiding. Hiding is one specific mechanic that makes use of Stealth checks. Some of these suggestions are great alternatives for the party to try, but the party is trying to Stealth so I'm not sure if the frame challenge is useful. It doesn't sit right to me to tell the party "instead of stealthiness, try convince the guests!". \$\endgroup\$ – user-63873687 May 30 at 2:53
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    \$\begingroup\$ Isn’t stealth all about blending in? Literally “not being seen” would be a very noticeable humanoid-shaped black silhouette. \$\endgroup\$ – Michael May 31 at 6:40
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A Stealth check is appropriate for this, but probably Charisma (Stealth) as opposed to the usual Dexterity (Stealth). It should probably be opposed by a Perception or Insight check on the pursuers part.

Stealth is described as (emphasis mine):

Make a Dexterity (Stealth) check when you attempt to conceal yourself from enemies, slink past guards, slip away without being noticed, or sneak up on someone without being seen or heard.

You might, in this case, change the base ability required for the stealth check to something more appropriate, like a Charisma (Stealth) check. The DMG specifically allows for this in the section on Using Ability Scores:

Under certain circumstances, you can decide a character’s proficiency in a skill can be applied to a different ability check. For example, you might decide that a character forced to swim from an island to the mainland must succeed on a Constitution check (as opposed to a Strength check) because of the distance involved. The character is proficient in the Athletics skill, which covers swimming, so you allow the character’s proficiency bonus to apply to this ability check. In effect, you’re asking for a Constitution (Athletics) check, instead of a Strength (Athletics) check.

Often, players ask whether they can apply a skill proficiency to an ability check. If a player can provide a good justification for why a character’s training and aptitude in a skill should apply to the check, go ahead and allow it, rewarding the player’s creative thinking.

Why Charisma? Well Charisma is a measure of your personality. It states:

Charisma measures your ability to interact effectively with others. It includes such factors as confidence and eloquence, and it can represent a charming or commanding personality.

From what you have described, your characters are in a social situation, and one in which they need to interact with people (blending in to the point of non-notability is still interacting with the room).

This would be opposed by one of:

  • Insight

    Your Wisdom (Insight) check decides whether you can determine the true intentions of a creature, such as when searching out a lie or predicting someone’s next move. Doing so involves gleaning clues from body language, speech habits, and changes in mannerisms.

  • Perception [either Wisdom (Perception) or Charisma (Perception)]

    Your Wisdom (Perception) check lets you spot, hear, or otherwise detect the presence of something. It measures your general awareness of your surroundings and the keenness of your senses.

  • Investigation:

    When you look around for clues and make deductions based on those clues, you make an Intelligence (Investigation) check.

  • An Intelligence or Charisma (Survival) check
    • Intelligence for making deductions, or Charisma for how well someone could read the room.
    • Survival for following someone through a crowd (akin to tracking someone using their footprints, you track them by other people's reactions to them)
    • Wisdom (Survival) may even still be appropriate here.

So what caused the weird disconnect?

The bit that caused the problem, and was likely inappropriate is the Pass without a Trace spell. It's designed specifically for dark situations where silence is key.

Pass without a Trace states(emphasis and emphasis mine):

A veil of shadows and silence radiates from you, masking you and your companions from detection. For the duration, each creature you choose within 30 feet of you (including you) has a +10 bonus to Dexterity (Stealth) checks and can't be tracked except by magical means. A creature that receives this bonus leaves behind no tracks or other traces of its passage.

Pass without a Trace, in an urban setting, coincidentally makes you cause a significant disturbance in a crowd (as opposed to just regularly walking through a crowd). Imagine you were a commoner and a shadowy, indiscernible, mass of figures surrounds you making no sound (as the characters walk around you). What are you going to do...probably scream your head off at the terrifying mass that is around you!

5e does not have fluff text, it is rules text all the way down. Pass without a Trace doesn't make you invisible. It doesn't make the people on the street beside you not see you. It makes you not disturb your surroundings, easier to hide in the shadows and not make any noise.

By making it a Charisma (Stealth) check you still allow the characters to use their Stealth skill, but Pass without a Trace no longer gives a bonus to the check as it's not Dexterity (Stealth).

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    \$\begingroup\$ I like the use of insight to spot the PCs, makes a lot of sense considering their actions. Cha (stealth) is a good idea too. I'm not sure about interpreting Pass without a Trace that way though. It adds +10 to stealth, so I doubt it makes you stand out so obviously. I think your interpretation is a little over the top and exaggerated :P \$\endgroup\$ – user-63873687 May 30 at 3:00
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    \$\begingroup\$ @user-63873687 it adds +10 specifically to Dexterity (Stealth) checks, not to stealth in general. \$\endgroup\$ – illustro May 30 at 8:38
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    \$\begingroup\$ correct, which is why I think it's hard to argue that it actually makes you less stealthy! \$\endgroup\$ – user-63873687 May 30 at 8:45
  • \$\begingroup\$ @user-63873687 passing unnoticed through a crowded room, or in a busy street at daytime is an entirely different prospect to sneaking through a house at night. That's why I suggested Charisma was the more appropriate ability to combine with Stealth rather than its usual Dexterity. It would not apply the +10 to a Charisma (Stealth) check. \$\endgroup\$ – illustro May 30 at 8:49
  • \$\begingroup\$ it does change what the PCs are doing, but it's a good thing to suggest. As a DM I am hesitant to tell my PCs "you should do this instead", but it's definitely a creative and effective idea. I don't think that was what the players had in mind, but in real life it works, so in game it should too! \$\endgroup\$ – user-63873687 May 30 at 8:59
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Pass without trace probably wouldn't help

a sniper camo suit

Does this camo suit make you more stealthy? I bet it does.

Would it help you to blend in with crowds better? I don't think so.

But let's start with the basics first.

The DM should always explicitly ask for checks

One of them cast pass without trace and they all rolled for Stealth

Why did they roll? In 5e the only way would be the DM asksing "make a X check", and the DM shouldn't ask for the Dexterity (Stealth) check before characters actually do something sneaky. I think this is the primary thing you made "wrong", all other is just a follow-up.

Characters do not "use skills" in 5e anymore. Actions like "I use my stealth skill" followed up by a inevitable dice roll was the 3.x thing. In 5e players describe, what their character do, then DM can optionally ask for a dice roll, then DM describes the outcome. This is how the game is described in the "How to play" chapter of the PHB.

So, in this case, you should ask "what do you do", "how do you do that", "what are you trying to accomplish". Then players describe, what their characters do and why. Then you describe the outcome. Maybe you won't ask for any check in the process, it is perfectly fine according to the DMG.

One of them cast pass without trace... They then proceeded to "sneak" past guests

How do I adjudicate this?

You follow the spell description. It says "A veil of shadows and silence radiates from you". Since there is no ignorable text in 5e spells, this is the part of the spell effect. So the characters followed by magical "veil of shadows and silence" enter the crowd. I doubt this could stay unnoticed, unless common people in your world are blatantly ignorant about magic.

The same problem would arise for me if they wanted to escape someone following them in a dense marketplace or in a crowded tavern. How can you Hide/roll for Stealth in a crowd

DMG suggests Dexterity (Stealth) check with advantage, see page 253 "Ending a Chase". It also says "Other factors might help or hinder the quarry's ability to escape, at your discretion". Ultimately it is up to you, the DM, as long as you follow the common sense and be consistent in your adjudications.

Summary:

  • You ask for a check, not players
  • Ask for a check when the consequences are imminent; do not ask beforehand
  • When you hesitate, ask players for clarifications. "How do you do that?"
  • Pay attention to details in spell descriptions; they might give a hint about how the spell works
  • "Dexterity (Stealth)" is fine, also is "Charisma (Stealth)" or any other ability check; RAW you can't choose "wrong" check here — ultimately it's up to the DM, use common sense when adjudicating ability checks; you might also not to ask for a check at all
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  • \$\begingroup\$ Good answer. I feel like the effects of pass without trace are probably not easily distinguishable. I mean, the spell is supposed to make you less noticeable, so having it make you incredibly conspicuous sounds wrong to me! \$\endgroup\$ – user-63873687 May 30 at 2:57
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    \$\begingroup\$ @user-63873687 well, wearing a sniper camo suit definitely makes you more noticeable at parties \$\endgroup\$ – enkryptor May 30 at 11:32
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    \$\begingroup\$ I asked them for a Stealth roll, I should have clarified. They basically said: "We want to sneak/move past the guests to the upper floor" and I asked them for a Stealth roll to do so, questioning myself if that was the right call afterwards. Nevertheless, you make some good points! \$\endgroup\$ – John W. May 30 at 13:59
  • \$\begingroup\$ @JohnW. According to the question body, the players rolled first, only then they described their actions ("proceeded to sneak past guests"). If this wasn't the case, please edit the question. \$\endgroup\$ – enkryptor May 30 at 16:39
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    \$\begingroup\$ @enkryptor OP edited the question to address the above comment \$\endgroup\$ – illustro May 31 at 23:18
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A Charisma (Deception) vs Wisdom (Insight) check

I'm guessing that you're referring to a certain location in Storm King's Thunder. If I'm right, the book suggests the following on page 216:

The adventurers might try to replace one or more of the workers [of the Grand Dame] [...] A character who wants to get aboard in this fashion must succeed on a Charisma (Deception) check contested by Captain Storn's Wisdom (Insight) check. A character who wins the contest can board the ship without raising suspicion.

The informational text on this page is talking about getting on board from the docks while it is tied up between trips, not getting into the CREW ONLY sections of the ship while it is underway and entertaining guests onboard but I think the Charisma (Deception) vs Wisdom (Insight) check works for both situations.

It might not be the Captain's Insight they are trying to oppose but that of whomever sees them attempting to access the off limits areas. This could be a crew member or the pit boss Pow Ming).

Even if I'm totally wrong on the campaign, I think the recommendation is still universally applicable.

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Stealth fits the situation

The Stealth section lists the situation you describe as an example:

Make a Dexterity (Stealth) check when you attempt to conceal yourself from enemies, slink past guards, slip away without being noticed, or sneak up on someone without being seen or heard.

We can see that 3 out of 4 of the examples listed under this skill directly apply to the situation you are describing. The players are concealing themselves, slinking past guards, and slipping away without being noticed. It's a perfect fit. Clearly, Stealth is the right choice for this situation.

Taking ques from Hiding

Hiding is a mechanic that uses Stealth checks. The abridged version of hiding is: roll a stealth check, enemies contest this with their passive perception, or with their perception if they make an active attempt. Until enemies succeed this check (or the hider leaves hiding), they can't be seen. It would be reasonable to use something similar in this situation too.

Your players rolled well, and the (perhaps intoxicated and distracted) party guests weren't too observant. It doesn't sound like anyone was particularly suspicious of the PCs, and so no one was actively hunting them. The plan has succeeded. Good job players!

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  • \$\begingroup\$ slink past implies avoiding being seen at all, as opposed to disguising yourself so they see you but don't see a problem. It could be possible to actually stealth past guards in a crowd, ducking behind people, but you'd set the DC much higher because any guard that does spot you moving this way around a room will think you look suspicious. So you have to avoid being seen at all by every guard all the time. \$\endgroup\$ – Peter Cordes Jun 1 at 0:34
  • \$\begingroup\$ @PeterCordes YMMV on that one. "Slink" as I understand it is more about moving smoothly and steathily in general, particularly moving quietly. In this situation it would be about not attracting attention, rather than not being seen. Note that hiding is just 1 mechanic that utilizes stealth, it isn't meant to encompass all uses of stealth. \$\endgroup\$ – user-63873687 Jun 1 at 2:57
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There are some clear rules concerning hiding in the PHB:

The GM decides when circumstances are appropriate for hiding.

And

You can't hide from a creature that can see you clearly.

When you find that waiting for an opportune moment to slip past someone is appropriate, that is covered by the rules. It is also worth noting that an opportune moment is probably one when there is specifically no person looking in the exact relevant direction. From your question I gather that the players need to conceal their entry to the forbidden areas and not their presence in general.

Additionally, Pass without Trace is a one hour concentration spell giving a bonus to stealth for the duration. It does not say that the check must be made immediately. Therefore, you can also demand the check as they enter a forbidden area. In that case, sneaking through the crowd is unnecessary.

If there is ever, realistically, a moment when no one looks in a specific direction would depend on the number of people in the room (unless a distraction was provided). But this is not clearly ruled by the book and you can decide this as the GM.

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    \$\begingroup\$ I think you are confusing Stealth with Hiding. Hiding is a mechanic that uses Stealth checks,. \$\endgroup\$ – user-63873687 May 30 at 2:55

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