Sneaking through areas people are watching closely

Question

If a Rogue is attempting to sneak (stealth) past 3 Orcs who are standing guard watching that very place, can this Rogue sneak past with a disadvantaged stealth attempt?

Do the orcs get a chance at Passive Perception to see the Rogue sneaking (using stealth skill)?

Do we roll/check for the Sneak and the Orcs get to check Passive Perception?

Context: The Rogue's speed is 25 feet (Dwarf/light armor), or 6 squares on the map and that gets him right near the orcs, but not past them, so the orc should get a Passive Perception check before the Rogue gets to move another 6 squares past them. Is this correct?

Answer 1

TL;DR

The rogue makes a single Dexterity (Stealth) check against a DC15 passive Wisdom (Perception). Beat that and the rogue gets past.

What the rules say about hiding

Stealing large chunks from my answer to What advantages does hiding have?

Best to go back to the source on this; bold italics are my emphasis.

PHB p.177

Stealth. 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.

PHB p.177

Hiding

When you try to hide, make a Dexterity (Stealth) check. Until you are discovered or you stop hiding, that check’s total is contested by the Wisdom (Perception) check of any creature that actively searches for signs of your presence.

You can’t hide from a creature that can see you, and if you make noise (such as shouting a warning or knocking over a vase), you give away your position. An invisible creature can’t be seen, so it can always try to hide. Signs of its passage might still be noticed, however, and it still has to stay quiet.

In combat, most creatures stay alert for signs of danger all around, so if you come out of hiding and approach a creature, it usually sees you. However, under certain circumstances, the Dungeon Master might allow you to stay hidden as you approach a creature that is distracted, allowing you to gain advantage on an attack before you are seen.

Passive Perception. When you hide, there’s a chance someone will notice you even if they aren't searching. To determine whether such a creature notices you, the DM compares your Dexterity (Stealth) check with that creature’s passive Wisdom (Perception) score, which equals 10 + the creature’s Wisdom modifier, as well as any other bonuses or penalties. If the creature has advantage, add 5. For disadvantage, subtract 5.

For example, if a 1st-level character (with a proficiency bonus of +2) has a Wisdom of 15 (a +2 modifier) and proficiency in Perception, he or she has a passive Wisdom (Perception) of 14.

What Can You See? One of the main factors in determining whether you can find a hidden creature or object is how well you can see in an area, which might be lightly or heavily obscured, as explained in chapter 8.

PHB Errata

The DM decides when circumstances are appropriate for hiding. Also, the question isn't whether a creature can see you when you are hiding. The question is whether it can see you clearly.

PHB p.183

A given area might be lightly or heavily obscured. In a lightly obscured area, such as dim light, patchy fog, or moderate foliage, creatures have disadvantage on Wisdom (Perception) checks that rely on sight.

A heavily obscured area—such as darkness, opaque fog, or dense foliage—blocks vision entirely. A creature in a heavily obscured area effectively suffers from the blinded condition (see appendix A).

Note: Blindsight is dim light and results in a lightly obscured area. Torches, lanterns etc are bright light.

Being seen is not enough for you to stop being hidden - you must be seen clearly. Lighting, cover and camouflage would all influence this.

Your specific questions

1. ... can this Rogue sneak past with a disadvantaged stealth attempt?

   Yes and furthermore I can see no reason why there would be disadvantage to this. Anyone can hide where nobody can see them; the purpose of the Dexterity (Stealth) skill is to be able to hide where people can see you due to your skill, training and luck.

2. Do the orcs get a chance at Passive Perception to see the Rogue sneaking (using stealth skill)?

   Yes - if the rogue's Dexterity (Stealth) check beats the orc's passive Wisdom (Perception) then he sneaks past them.

3. Do we roll/check for the Sneak and the Orcs get to check Passive Perception?

   Exactly.

4. The Rogue's speed is 25 feet (Dwarf/light armor), or 6 squares on the map and that gets him right near the orcs, but not past them, so the orc should get a Passive Perception check before the Rogue gets to move another 6 squares past them. Is this correct?

   No, because:

   1. 25 feet is 5 squares on the map (just saying).

   2. You do not use round by round movement unless you are in a combat situation so if the rogue sneaks past then he sneaks past, if he doesn't you may be rolling initiative and switching to round by round movement then.

   3. There is no passive [Wisdom] (Perception) check - it is a static number; for an orc it is 10.

      Effectively the rogue makes a Dexterity (Stealth) check against a DC of 15 (10 for orc's passive Wisdom (Perception) + 5 for advantage because there is more than one orc doing the looking and they therefore help one another), if the area is brightly lit and there is no cover.

      If there are sufficient objects/people to hide behind or it is dimly lit (which includes darkvision) then the DC is 10 as the disadvantage for lightly obscured cancels the advantage from helping.

      If the rogue is doing it in the dark (and he can see somehow) then it is automatic; barring making a noise.

Why not use active Wisdom (Perception)

Because the orcs are "standing guard" which to me does not engage "actively searches for signs of your presence." Standing guard is long, boring duty and you are not going to pay attention all the time especially when you have a couple of mates around to chat with.

If they were in a state of heightened alertness (like they knew you were out there right now!) then they could use active Wisdom (Perception).

Answer 2

Remember that as the GM, you always have the authority to say "no".

If this is the case, you should tell the player first and let them decide. "The area is well-lit and well watched, you think it is impossible to sneak through." If the player still wants to sneak, then just tell them "your character is spotted" and run it from there. No dice roll (there is no rule that says "players must have a chance to roll a die.").

If you decide that success is possible, then run a skill contest - the player's DEX (Stealth) roll against the Orcs' WIS (Perception) rolls. If the player (one roll) beats all the orcs (three rolls) then they make it else they are spotted.

If the area is particularly well lit or the Orcs are particularly watchful then give the player disadvantage. If the area is particularly badly lit or the Orcs are particularly inattentive then give the player advantage. If the character has magical help (for example, invisibility) then give the player advantage.

If you want to make it a little more likely for the player to succeed then only roll once for the Orcs' WIS (Perception).

Either way, the player only rolls once.

Answer 3

This would be a Skill Contest. The guards are actively looking for intruders while on duty. So they aren't passive and therefore do not use Passive Perception, instead they get a roll for Perception. Depending on the number of entrances, or how the player wishes to sneak past, they may or may not have disadvantage. I believe this would be left up to the GM to decide unless they use a spell or ability that grants them an advantage on a stealth check.

As a GM, if the player is trying to sneak into an area guarded by 3 orcs, I would rule disadvantage, since he would be sneaking right past them, or through an area they can see well if they are maybe in a tower or something.

The rogue wants to sneak past the guards, so she rolls stealth (possibly with disadvantage, GM rule in my opinion). The guards are actively looking so they roll for perception (you could roll one check as a group for the guards or roll separately per guard).

So both the GM and the Player roll, compare their numbers, and the highest number succeeds.

Answer 4

Passive Perception is used only when a creature is not actively trying to notice something. If a creature is guarding an area than generally they are meant to be looking out for signs of danger, intruders, or what-have-you, and thus they are actively trying to notice something. As such, they're not using their Passive Perception and would get to roll a Wisdom (Perception) check that would be contested by the Rogue's Dexterity (Stealth) check.

It's also worth noting that each orc would roll a separate perception check to be contested by the rogue's one stealth check.

Whether the rogue makes their stealth check with disadvantage or not is dependent on a number of factors and is ultimately left up to DM discretion.

Scarcity of places to hide, number of entry points, how well an area is lit, whether the rogue is up wind or down wind, and even proximity to the guards could all impose disadvantage to a stealth check if the DM wishes it but just as easily, player tactics and DM co-operation could either negate that disadvantage or even grant advantage to the stealth roll.