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So I've been DMing a 5e game lvl 1-3 so far. And I have a question about stealth for my rogue. My player has been hiding behind/stealthing behind another PC.

So this is what usually happens. PCs bust into a room, and the enemies see him. The rogue makes a stealth check and hides behind a PC as a bonus action, then attacks from stealth and gets sneak attack. He will do this every round. I do try to do Perception for the NPCs, but they fail. So he basically disappears for the whole encounter.

So then he attacks cause he is fully hidden and gets a sneak attack every time. This seems OP!! I thought you could only hide in full cover. I know the Skulker feat allows a player to hide in partial cover, which I looked up. Hiding behind a PC of medium size only allows partial cover. Please help me! I just wanna make sure I'm doing this right and I hate players who take advantage of a loop hole.

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You are correct: generally, you cannot hide behind another PC or creature and make a Stealth check.

However, lightfoot halflings can do so (they make great rogues for this reason), if the creature is one size larger than them (which includes Medium-sized PCs).

The Skulker feat (PHB, p. 170), though, does not allow hiding behind PCs. It allows hiding in "lightly obscured" areas, but no other situations (beyond the normal stealth rules). PCs provide half cover, but no obscurity, so Skulker does not apply.

Also, remember that the rogue needs to use either their action or bonus action to Hide (other characters can only use their action to do so). This means that they can't effectively use Two-Weapon Fighting and hide regularly.

Ultimately, this merely allows the rogue to get her Sneak Attack off every turn. Contrary to what you are thinking, this is not overpowered in any way. This is the rogue working as designed.

At low levels, the rogue can be quite good, especially when you factor in advantage. However, as you level up, the rogue's damage, because it always depends on the single attack, will fall off the table compared to other classes.

So, while this may seem overpowered, rogues are supposed to be able to get advantage fairly easily, and to be able to perform Sneak Attacks on pretty much every turn; this is the only way they can consistently compete for damage, especially as things level up.

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    \$\begingroup\$ Doesn't hiding take an action? Also, maybe mention that you get sneak attack just by having an ally next to the target (not advantage though). \$\endgroup\$
    – firedraco
    Apr 24, 2015 at 18:47
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    \$\begingroup\$ @firedraco rogues can do it as a bonus action. \$\endgroup\$
    – wax eagle
    Apr 24, 2015 at 18:47
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    \$\begingroup\$ Can you clarify this sentence -- I can't parse it: "It allows hiding in "lightly obscured" areas, which is not the case where there is half cover, but no other situations." \$\endgroup\$ Apr 25, 2015 at 1:28
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    \$\begingroup\$ @PurpleVermont "Skulker allows hiding in 'lightly obscured' areas (but half cover is not lightly obscured) and does not give bonuses in other situations" \$\endgroup\$ Nov 20, 2019 at 9:21
  • \$\begingroup\$ Consider adding the distinction between cover and obscured. Specifically, cover is how hard it is to target something, which is reflected through AC in an attempt to hit them. Obscured is how hard it is to see them, and usually revolves around lighting or forms of camouflage. A lot of the time, there's a ton of overlap and the distinction is subtle. Example, a party inside a fog cloud is heavily obscured, but not behind cover. Whereas a party inside a tower is behind total cover while also heavily obscured. \$\endgroup\$ Jun 26 at 16:19
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First off, what the rogue is doing may be unnecessary, as all he needs to do to satisfy the conditions for a Sneak Attack is to have an ally within 5 feet of the target. Having advantage on the attack (e.g. from being unseen) is only one way to generate a Sneak Attack on a target.

Secondly, the Rogue is not able to hide behind a PC, due to the rules on hiding:

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.

Once the Rogue is spotted by a creature, he cannot hide from the creature unless he breaks line of sight.

Ducking behind a character does not count as breaking line of sight. It only provides half cover:

A target with half cover has a +2 bonus to AC and Dexterity saving throws. A target has half cover if an obstacle blocks at least half of its body. The obstacle might be a low wall, a large piece of furniture, a narrow tree trunk, or a creature, whether that creature is an enemy or a friend.

There's one exception to this: Lightfoot Halflings can hide behind other characters due to their Naturally Stealthy racial trait:

You can attempt to hide even when you are obscured only by a creature that is at least one size larger than you.

But remember: this doesn't exempt them from the observation rule.

The best bet for the Rogue character is to wait until one of his allies is within 5 feet of his target before launching a Sneak Attack.

Thirdly, the Cunning Action feature lets rogues Hide as a bonus action, not a free action. A minor point, but its use precludes the use of any other ability that can be used with a bonus action (like a second weapon attack with Two-Weapon Fighting).

As a final note, frequent Sneak Attacks are expected to occur often with the Rogue. This may seem overpowering compared to the fighter. However, the Rogue has a single devastating attack, while a fighter is able to generate multiple attacks.

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    \$\begingroup\$ Re: "Hide for Rogue is a bonus action not a free action". Looking over these 5E rules, trying to understand. It doesn't look like 'free action' is even a concept in this edition. Looks like 'Hide' is normally an 'action', like attacking, but rogues can do it as a 'bonus action' or a normal action. Right? \$\endgroup\$
    – DCShannon
    Apr 24, 2015 at 20:19
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    \$\begingroup\$ @DCShannon correct. You get the following in a round of combat. 1 Action, 1 Bonus Action, 1 Reaction, 1 Interaction. You can't freely exchange Bonus Actions with Actions. What allows the Rogue the choice is the fact Hide is a actions for all characters but the Rogue has a class feature that allows him take a Hide Action as a bonus action. \$\endgroup\$
    – RS Conley
    Apr 24, 2015 at 21:33
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    \$\begingroup\$ I read the halfling’s ability as satisfying all of the qualifications for hiding, just by getting “lost” underfoot. Your way of reading it is reasonable too, but I prefer the more generous reading. \$\endgroup\$ Apr 24, 2015 at 23:16
  • \$\begingroup\$ "But remember: this doesn't exempt them from the observation rule." - I disagree with this reading. Being observed is the only thing that stops you from being able to [attempt to] hide; Naturally Stealthy says "you can attempt to hide when ...", therefore it must be overriding the general rule requiring you to be unseen to hide. Otherwise it would literally do nothing. \$\endgroup\$ Jul 27, 2022 at 10:37

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