How do you handle plain sight while sneaking?

Question

As I understand it, once a character successfully rolls a Dexterity (Stealth) ability check, they are successfully hidden and moving stealthily. Others will need to succeed on a Wisdom (Perception) check or have a high enough passive perception to detect them.

The rules also declare that you cannot hide in plain sight ("you cannot hide from a creature that can see you clearly"), but on the other hand, the rules treat everyone as having 360 degree vision in combat.

Does that mean there would be no way to sneak by a guard that logically has to look the other way from time to time to cover that full range of vision, even if it would be for only a short stretch of ground, or that you cannot sneak up to attack someone if there is any amount of open-view space you have to clear for doing so? When does being hidden end automatically?

Answer 1

You've made an absurd assumption

Which you are perhaps intending to do, to make a point.

You statement, "The rules treat everyone as having 360 degree vision in combat" is just not true or supportable.

You make a further incorrect assumption (again, perhaps to prove a point), that rules for sneaking in combat apply out of combat; for instance, when sneaking past a guard.

So, your two false assumptions:

• The rules of sneaking in combat grants 360 degree vision
• The rules of sneaking in combat apply out of combat

In combat

The rules on hiding on combat say (Basic Rules, Chapter 7, Dexterity, sidebar "HIDING"; emphasis added):

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 DM might allow you to stay hidden as you approach a creature that is distracted, allowing you to gain advantage on an attack roll before you are seen.

Note the qualifiers I highlighted. This does exactly the opposite of treating everyone as if they have 360 degree vision in combat. It's saying, "usually you can't sneak up on someone in combat, but sometimes you can" . . . "usually creatures are looking around, but sometimes they aren't".

So, even in combat, the rules do not treat everyone as having 360 degree vision.

The phrase "most creatures stay alert for signs of danger all around" is providing a default narrative for combat. Most creature stay alert, but there could be exceptions. This specifically does not address hiding or sneaking outside of combat.

Outside of combat

As you mention, outside of combat, the rules provide support for a stealth check (Basic Rules, Chapter 7, Dexterity):

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.

It's up to the DM to provide the narrative support for the stealth check. The narrative details of concealing yourself, slinking past guards, slipping away, or sneaking up will determine how difficult the check is.

It's worth recalling that DC stands for "difficulty class", and the rules relate it back to broad categories of "very easy" to "nearly impossible", and furthermore, that the DM can impose multiple checks as necessary, which, of course increases the difficulty.

Fine points need to be adjudicated by the DM

Exactly how the stealth check plays out, the DM needs to adjudicate. It's not a video game -- the narrative matters. A guard might be attending to duty and staring fixedly over the rampart, in which case, they aren't looking behind them. In a different situation, a guard might be much more likely to look behind on occasion; up to the DM, as is how often they look behind.

If the guard doesn't look, they can't see you

If you're sneaking past a guard by sneaking behind them, and they don't look, then they can't see you.

Maybe in that case the DC is 15, "medium", or perhaps higher or lower depending on circumstances. If another party member provides a distraction, the DM can alter the DC, or choose to provide advantage on the stealth check.

If the guard looks, and you're right there in "plain sight", you're no longer hiding

However, if for whatever reason, the guard turns around, and they can see you, then they see you. It's that simple.

Unless there are extenuating circumstances, you're in "plain sight", and you're seen.

Your specific questions

You ask, "Does that mean there would be no way to sneak by a guard that logically has to look the other way from time to time to cover that full range of vision...?"

The DM needs to adjudicate. The rules don't and can't give hard and fast rules for that, and neither can we.

About sneaking up on someone

You go on to ask, "...you cannot sneak up to attack someone if there is any amount of open-view space you have to clear for doing so?"

The DM needs to adjudicate. The rules don't and can't give hard and fast rules for that, and neither can we.

When does being hidden end automatically?

You finally ask, "When does being hidden end automatically?"

It ends when you're detected.

In case more evidence is needed

The rules assume non-360-degree vision. An example is the stealth check quote above, ". . . sneak up on someone without being seen . . .". If the rules assume 360 degree vision, then that phrase makes no sense.

There are other places as well. For instance, the description of the medusa says:

Unless surprised, a creature can avert its eyes to avoid the saving throw at the start of its turn.

If the rules assume 360 degree vision, then "avert its eyes" is weird.

How to handle it as a DM

I feel like there's a subtext to your questions; somehow the rules have let you down, and it's not clear why. It may be that in some circumstance your DM and players aren't seeing eye-to-eye. That might be the real issue.

However, I can tell you how I handle similar situations, and how other DMs in my group handle it.

As you know, the rules say:

The stealth rule quoted above is a pretty good general-purpose rule. Depending on the circumstances, someone attempting to sneak past a guard, I might have them make a stealth check and be done with it. I might set the DC differently depending on circumstances. I might grant them advantage.

The DM needs to decide what level of detail to focus on. Is this a simple check? Maybe a stealth roll is all you need and you don't need to drill into which way the guard was looking. Or maybe you want to drill into it further, "as you spy on the guards, you are pretty sure you can't just slip past when they aren't looking. You can try, but it seems dubious."

So . . . case-by-case, make it interesting, make it challenging, choose level of focus, make a ruling, move on.

Answer 2

The rules dictated in the hiding sidebar do not neccessarily apply to a stealth check made to sneak past guards.

"Hiding," inasmuch as it has any rules definition, is solely remaining completely undetected by a target. If you attempt to hide in combat, your character can usually not be in plain sight, although, as specified in the PHB, DMs can always make an exception to that rule. Generally speaking, a person in combat will see your hiding character dash across even that 5-foot gap in the fence, as you cannot hide in plain sight.

However, if the person you want to sneak past is not in combat, you are allowed to say whatever you think could get you past them, and the DM will call for a Dex(stealth) roll if they think it's legitimate and applicable. Statements such as "I crouch behind the fence and dash as quickly as possible between the gaps, hoping that the guard only sees a flickering shadow," or "I try to covertly watch the guard, and dash between the gaps in the fence when he yawns or looks away," both work to sneak past without having anything to do with the hiding rules.

Answer 3

During combat creatures are usually alert

The rules for hiding on PHB p. 177 explain that once you successfully roll stealth, you are hiding "until you are discovered or stop hiding". Of course in this circumstance you would not want to stop hiding. So the question is when exactly are you discovered. This depends on how alert the creature you are hiding from is. The box explains further:

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.

So during combat it is generally assumed that the combatants have '360° Vision' and you would typically be discovered immediately if you leave your hiding spot and are no longer obscured. This is actually kind of similar to how Attacks of Opportunity work, even if someone behind you is leaving your range you would still see them and be able to attack them with your reaction.

But your DM is explicitly allowed to rule otherwise

Note though that the text says usually so there can be exceptions to this. This is explained in the next sentence:

[...] the DM might allow you to stay hidden as you approach a creature that is distracted

So if the Orc Warchief you are sneaking up on is currently busy slashing his axe at one of your other party members, your DM might decide he is too distracted to notice you approaching him, and you would then still be able to get the advantage on your attack roll from being hidden while attacking him, even after leaving cover and no longer being obscured.

The same principles would apply outside of combat

This paragraph clearly talks about combat. How this is handled outside of combat is not stated explicitly, but I think we can easily extrapolate that. It comes down to whether or not the creature you are hiding from is looking around attentively for any signs of danger all around them or looking distractly in one direction. Which is ultimately the decision of the DM.

In the example of sneaking past a guard, they would usually be attentive, atleast if they are good at their job. But maybe you can use your wits to distract them for a few seconds, like throwing a rock the other way to make a sound or having one of your party members engage them in conversation, so you can sneak behind them unseen.

Answer 4

"see you clearly" =/= "in plain sight"

This is where the rules break down as arguably being lightly obscured would be where you cannot be seen clearly yet the feat Skulker and the Mask of the Wild trait of Wood Elves (both in the PHB) talk as if no creature can use being lightly obscured to hide unless they had these traits.

I believe Skulker and Mask of the Wild are an oversight from when the hiding rules were changed in an errata.

"Hiding (p. 177). The following sentence has been added to the beginning of this section: “The DM decides when circumstances are appropriate for hiding.”

The first sentence of the second paragraph now begins, “You can’t hide from a creature that can see you clearly …”

It used to say "You can’t hide from a creature that can see you,"

Before that there was no special value on "see you clearly". The PHB was originally published with such extreme limitations on hiding that it was useless. Skulker and Wood Elf should be changed to have advantage when hiding when lightly obscured. It should not effectively prevent any other creature from even attempting to hide when lightly obscured.

With that in mind, the rules explicitly say on page 177 of the PHB:

if you come out of hiding and approach a creature, it usually sees you.

Emphasis added, usually sees you. This is not an absolute rule, it is a suggestion to the DM. The rules continue:

However, under certain circumstances, the DM might allow you to stay hidden as you approach a creature that is distracted, allowing you to gain advantage on an attack roll before you are seen.

The rules say there are certain unspecified circumstances AND an explicit stipulation of the creature you're hiding from being distracted.

So to answer your question, it's a three part test:

• Are the creature or creatures you're hiding from distracted?
• Does the totality of circumstances contributing to hiding?
• Does the DM allow it?

Then you can emerge from cover and approach a creature using Stealth to make an attack as an unseen attacker.

Just bear in mind the hiding rules are very broken in 5th Edition, there's lot of contradictions as the base rules were changed yet ancillary rules were not updated for the change. Any DM's work is cut out for them to account for these internal contradictions.