[RPG] Sneaking through areas people are watching closely

dnd-5estealth

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?

Best Answer

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).