Whenever you wish to use Stealth, you make a Dexterity (Stealth) check, and unless an enemy is actively searching for you OR your stealth does not beat the enem(ies) Passive Perception, you are in Stealth.
Stealth allows you to "conceal yourself from enemies, slink past guards, slip away without being noticed, or sneak up on someone without being seen or heard." (p.177 PH Stealth)
"When a creature can't see you, you have advantage on attack rolls against it. If you are hidden-both unseen and unheard-when you make an attack, you give away your location when the attack hits or misses." (p194-195 PH Unseen Attackers and Targets)
So Stealth has an obvious advantage and as any character, you'd like to be in stealth as much as possible, gaining advantage on your Attack (virtually the best way to increase damage in the game). You could consider yourself 'sneaking' whenever you are about to enter a combat situation you are aware of, either opening a door in a dungeon crawl or approaching enemies who don't see you first. The rules for Stealth are fairly clear, and lets assume you may often get this initial attack (and give away your location) but after that?
There is a defined action called 'Hide', which requires your Action (specific to combat). So this is clearly designed for in-combat use.
"When you take the Hide action, you make a Dexterity (Stealth) check in an attempt to hide, following the rules in chaper 7 for hiding. If you succeed, you gain certain benefits, as described in the "Unseen Attackers and Targets" section" (p.192 PH Hide)
Which directs us back to the rules on 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, you give away your position.... 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." (p.177 PH Hiding)
So, we now have a divide between Stealth, which allows us to move toward and attack enemies with advantage. And Hiding which cannot be used whenever any creature in combat can see you. However, if you somehow were not visible (line of sight) perhaps you could hide, but there is an implication that you aren't supposed to be able to move. And even if you do, the GM only affords you the benefit of sneaking 'under certain circumstances.'
[Rogue] The rogue specifically gains a special ability at Level 2 called 'Cunning Action'. This allows him to spend a bonus action on each turn to Dash, Disengage, or Hide. Implying that the rogue can use his Bonus Action to 'hide', and when successful, make an Attack while hidden and gain Advantage on that attack. However, this does not remove the limitations above that imply you cannot actually Hide when enemies can see you, and perhaps you cannot move. (Implied by "if you come out of hiding and approach a creature" which presumes that movement toward a creature would bring you out of your hiding place.)
So, while it seems at first glance the rogue can Hide as a bonus action with a Dexterity (Stealth) check Vs Passive Perception, and then Attack with Advantage, I don't believe it actually works.
[Lightfoot Halfling] The lightfoot halfling however, has an ability called 'Naturally Stealthy' which reads "You can attempt to hide even when you are obscured only by a creature that is at least one size larger than you." (p.28 Naturally Stealth). This implies that as long as a creature of medium size or larger is between you and your opponent, you CAN hide. Therefore, level 2 Rogue Lightfoot Halflings are able to spend a bonus action Hiding, and then attacking from their hidden position for Advantage on every attack, as long as a medium sized ally is next to them (and they don't ruin their hiding place by moving?).
[Vision and Obscurity] In the Hide section, it also states "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." (p.177 Hiding) And then in chapter 8 "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" (p.183 Vision and Light)
This states that while darkness and shadows might create a lightly obscured area, enemies can still see you (and deny your ability to hide) but you could Hide whenever you cannot see. However, not being able to see also blinds you, so your Advantage and Disadvantage could cancel each other.
Coverage follows in the same way, anything that would give you enough coverage to Hide, would also create enough coverage to apply disadvantage. If they cant see you, you cant see them. And if you cannot move after Hiding, it becomes mechanically moot in gaining combat advantage.
Initial Conclusion - I believe only a Lightfoot Halfling can repeatedly Hide and Attack for Advantage on his attacks. Every other case seems disqualified, since Hiding is unusable whenever an enemy can 'see' you, and you cannot move once hidden.
Counter-argument - Although the Hide and Sneaking rules have different disqualifications implying that they are 'different' nothing seems to openly admit that they were supposed to be two different things. And if all forms of Hiding are in fact Sneaking, the Sneaking rules clearly let you move and attack enemies with Advantage. Therefore, all Rogues may be able to Hide whenever they are out of line of sight, then move into vision, and make an Attack with Advantage. Every round that a rogue had a corner, or a pillar to get full coverage behind, they could split their move, go around the corner, Hide as a Bonus Action (at Level 2+) move back into vision, and Attack from Stealth with Disadvantage.
[Feats] Feats seem to further shed light upon this; [Alert] and [Skulker].
Alert says "Other creatures don't gain advantage on attack rolls against you as a result of being hidden from you." This implies that Hidden, Hiding, and Sneaking are all the same, since it would seem absurd that an opponent who was hiding would be deprived of this advantage, but an opponent who was sneaking toward you would not.
Skulker says "You can try to hide when you are lightly obscured from the creature from which you are hiding. When you are hidden from a creature and miss it with a ranged weapon attack, making the attack doesn't reveal your position" This feat would solidly allow you to Hide as a bonus action, and attack with Advantage, whenever you are lightly obscured. It also implies that Hiding and Sneaking are one and the same thing.
Please let me know your thoughts.
Stealth allows you to "conceal yourself from enemies, slink past guards, slip away without being noticed, or sneak up on someone without being seen or heard." (p.177 PH Stealth)
"When a creature can't see you, you have advantage on attack rolls against it. If you are hidden-both unseen and unheard-when you make an attack, you give away your location when the attack hits or misses." (p194-195 PH Unseen Attackers and Targets)
So Stealth has an obvious advantage and as any character, you'd like to be in stealth as much as possible, gaining advantage on your Attack (virtually the best way to increase damage in the game). You could consider yourself 'sneaking' whenever you are about to enter a combat situation you are aware of, either opening a door in a dungeon crawl or approaching enemies who don't see you first. The rules for Stealth are fairly clear, and lets assume you may often get this initial attack (and give away your location) but after that?
There is a defined action called 'Hide', which requires your Action (specific to combat). So this is clearly designed for in-combat use.
"When you take the Hide action, you make a Dexterity (Stealth) check in an attempt to hide, following the rules in chaper 7 for hiding. If you succeed, you gain certain benefits, as described in the "Unseen Attackers and Targets" section" (p.192 PH Hide)
Which directs us back to the rules on 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, you give away your position.... 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." (p.177 PH Hiding)
So, we now have a divide between Stealth, which allows us to move toward and attack enemies with advantage. And Hiding which cannot be used whenever any creature in combat can see you. However, if you somehow were not visible (line of sight) perhaps you could hide, but there is an implication that you aren't supposed to be able to move. And even if you do, the GM only affords you the benefit of sneaking 'under certain circumstances.'
[Rogue] The rogue specifically gains a special ability at Level 2 called 'Cunning Action'. This allows him to spend a bonus action on each turn to Dash, Disengage, or Hide. Implying that the rogue can use his Bonus Action to 'hide', and when successful, make an Attack while hidden and gain Advantage on that attack. However, this does not remove the limitations above that imply you cannot actually Hide when enemies can see you, and perhaps you cannot move. (Implied by "if you come out of hiding and approach a creature" which presumes that movement toward a creature would bring you out of your hiding place.)
So, while it seems at first glance the rogue can Hide as a bonus action with a Dexterity (Stealth) check Vs Passive Perception, and then Attack with Advantage, I don't believe it actually works.
[Lightfoot Halfling] The lightfoot halfling however, has an ability called 'Naturally Stealthy' which reads "You can attempt to hide even when you are obscured only by a creature that is at least one size larger than you." (p.28 Naturally Stealth). This implies that as long as a creature of medium size or larger is between you and your opponent, you CAN hide. Therefore, level 2 Rogue Lightfoot Halflings are able to spend a bonus action Hiding, and then attacking from their hidden position for Advantage on every attack, as long as a medium sized ally is next to them (and they don't ruin their hiding place by moving?).
[Vision and Obscurity] In the Hide section, it also states "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." (p.177 Hiding) And then in chapter 8 "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" (p.183 Vision and Light)
This states that while darkness and shadows might create a lightly obscured area, enemies can still see you (and deny your ability to hide) but you could Hide whenever you cannot see. However, not being able to see also blinds you, so your Advantage and Disadvantage could cancel each other.
Coverage follows in the same way, anything that would give you enough coverage to Hide, would also create enough coverage to apply disadvantage. If they cant see you, you cant see them. And if you cannot move after Hiding, it becomes mechanically moot in gaining combat advantage.
Initial Conclusion - I believe only a Lightfoot Halfling can repeatedly Hide and Attack for Advantage on his attacks. Every other case seems disqualified, since Hiding is unusable whenever an enemy can 'see' you, and you cannot move once hidden.
Counter-argument - Although the Hide and Sneaking rules have different disqualifications implying that they are 'different' nothing seems to openly admit that they were supposed to be two different things. And if all forms of Hiding are in fact Sneaking, the Sneaking rules clearly let you move and attack enemies with Advantage. Therefore, all Rogues may be able to Hide whenever they are out of line of sight, then move into vision, and make an Attack with Advantage. Every round that a rogue had a corner, or a pillar to get full coverage behind, they could split their move, go around the corner, Hide as a Bonus Action (at Level 2+) move back into vision, and Attack from Stealth with Disadvantage.
[Feats] Feats seem to further shed light upon this; [Alert] and [Skulker].
Alert says "Other creatures don't gain advantage on attack rolls against you as a result of being hidden from you." This implies that Hidden, Hiding, and Sneaking are all the same, since it would seem absurd that an opponent who was hiding would be deprived of this advantage, but an opponent who was sneaking toward you would not.
Skulker says "You can try to hide when you are lightly obscured from the creature from which you are hiding. When you are hidden from a creature and miss it with a ranged weapon attack, making the attack doesn't reveal your position" This feat would solidly allow you to Hide as a bonus action, and attack with Advantage, whenever you are lightly obscured. It also implies that Hiding and Sneaking are one and the same thing.
Please let me know your thoughts.
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