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All halflings have the Halfling Nimbleness feature:

You can move through the space of any creature that is of a size larger than yours.

Lightfoot Halflings have the Naturally Stealthy ability:

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

Halflings are sized small, while Dragonborn, for instance, are medium.

A rogue has a Cunning Action:

You can take a bonus action on each of your turns in combat. This action can be used only to take the Dash, Disengage, or Hide action.

And our group has been playing with a Barbarian Dragonborn and the Lightfoot Halfling Rogue. In combat, let's say, facing a single boss, the rogue usually hits and hides behind the Dragonborn (moving through him). A stealth check is rolled against the boss's perception, and if the boss wins, he can go around the barbarian and hit the rogue. He does not trigger attacks of opportunity because he is not leaving the barbarian's melee range.

However, for the rogue to go behind the dragonborn, he should trigger an opportunity attack from the boss, right? Or can the hide action include this 5 feet move to hide behind the dragonborn? Or does the nimbleness feature prevent attacks of opportunity, since the rogue can simply stand in the dragonborn's space, only behind him? Does standing in the same space as a bigger creature prevent attacks against you because the creature shields you?

In terms of RP and realism, we've been describing this as such: the halfling is hiding in the back of the barbarian, pops out to strike, and hides back there. The idea here is to have the rogue safely out of harm's way (dumb enemies won't understand where he is, others will attack with disadvantage, and others will actually have to move to him him (unless they're grappled).

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  • \$\begingroup\$ "Does standing in the same space as a bigger creature prevent attacks against you because the creature shields you?" The DM may allow you to gain cover (+2 AC), similar to when a creature is between you and the attacker. \$\endgroup\$ – Doval Dec 23 '16 at 23:12
  • \$\begingroup\$ I don't understand 'proc an opportunity attack'. Please edit to either reword or explain what proc means. \$\endgroup\$ – Clearly Toughpick Dec 24 '16 at 9:12
  • \$\begingroup\$ @ClearlyToughpick Fixed \$\endgroup\$ – BlueMoon93 Dec 24 '16 at 14:06
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It seems the problem you're trying to solve, is how to get consistent Advantage on attacks, without provoking opportunity attacks. This depends on a number of things.

What is the boss's reach? If the boss's reach is longer than 5 ft, then you will not provoke an opportunity attack to move behind your Dragonborn friend, if he is within 5 ft of the boss.

Must you use melee attacks? Using ranged weapons in a different location would be much safer, keeping you farther from the Boss, protecting you from Area of Effect spells or abilities, and giving you Advantage consistently without having to worry about disengaging.

You're also making a few assumptions:

  1. Hiding means you are completely undetectable. This is false. He can't currently see you, and you have advantage to hit the boss, but for an intelligent creature, it's pretty obvious you're behind the Dragonborn somewhere, and he can still move around your friend to spot you. Additionally, barring the Skulker feat, attacking will reveal you. Also, simply stepping out from behind the Dragonborn will reveal you if the Boss is looking in your direction. (Also note there are no facing rules in fifth edition by default, so this is subject to GM rulings) Note this makes hiding in melee rather impractical without specialized abilities.
  2. Nimbleness means you can stand in another creature's space. You may pass through another creature's space, but you may never end your turn in another creature's space, unless they are multiple size categories larger than you.

As it stands, the Rogue does not have enough actions to Disengage, Hide, AND Attack in one turn, so he would either provoke an opportunity attack, or not be able to attack. The alternative that would allow Advantage attacks every turn, is to use a ranged weapon, and hide at a distance.

Note, if all you're concerned with is getting your sneak attack bonus, all that is required is either having advantage or an allied creature is within 5 ft of your target. Keep in mind that applies to ranged or melee attacks: so as long as the Dragonborn is next to the boss, the Rogue will still get sneak attack against it.

Unseen Attackers and Targets (Fifth Edition SRD)

Combatants often try to escape their foes’ notice by hiding, casting the invisibility spell, or lurking in darkness.

When you attack a target that you can’t see, you have disadvantage on the attack roll. This is true whether you’re guessing the target’s location or you’re targeting a creature you can hear but not see. If the target isn’t in the location you targeted, you automatically miss, but the GM typically just says that the attack missed, not whether you guessed the target’s location correctly.

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.

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  • \$\begingroup\$ Comments are not for extended discussion; this conversation has been moved to chat. \$\endgroup\$ – SevenSidedDie Dec 23 '16 at 20:38
  • \$\begingroup\$ simply stepping out from behind the Dragonborn will reveal you if the Boss is looking in your direction. He could attack from the Dragonborn's space as long as he moves out of that space afterwards; the rules say "Whether a creature is a friend or an enemy, you can't willingly end your move in its space." So if the DM rules that he counts as obscured while he's in the Dragonborn's space and the Dragonborn is next to the enemy, he could: start the turn hidden behind his friend -> move into his friend's space -> attack -> hide -> move back behind his friend. \$\endgroup\$ – Doval Dec 23 '16 at 23:10
  • \$\begingroup\$ @Doval Sage Advice disagrees with that assessment, and even if it was true, he would still provoke opportunity attacks. Whether he becomes unhidden or not in that situation is entirely up to DM judgement. \$\endgroup\$ – Randomorph Dec 24 '16 at 0:36
  • \$\begingroup\$ @Randomorph he would still provoke opportunity attacks he wouldn't provoke if he succeeds on the hide check (creatures you can't see don't provoke opportunity attacks). But I didn't account for Crawford's tweet on the subject of attacking from another creature's square, so my suggestion doesn't work regardless. Good catch. \$\endgroup\$ – Doval Dec 24 '16 at 1:53
  • \$\begingroup\$ @Doval you cannot hide from a creature that can see you, so you would have to move out of view first, before hiding. \$\endgroup\$ – Randomorph Dec 24 '16 at 1:55
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Use Cunning Action to take the Disengage action

The set up:

  • The Barbarian is standing in front of a Boss
  • The Rogue is standing behind the Barbarian
  • The Rogue has already taken the Hide action, and the DM has determined that the Rogue's Stealth check has beaten Boss's Passive Perception.

The play by play:

  1. The Rogue moves forward 5ft into the Barbarian's square
  2. The Rogue attacks the Boss with advantage since they are Hidden
  3. The Rogue uses Cunning Action to take the Disengage action
  4. The Rogue moves back behind the Barbarian, and does not provoke an Attack of Opportunity

At the end of this play the Rogue is back where they started, behind the Barbarian, and is still Hidden. If at some point the Boss takes the Search action and discovers the Rogue, the Rogue would need to back off and Hide again, breaking their rhythm.

Note the following potential mechanics misunderstandings:

  • A creature taking the Hide action is actively trying to be sneaky. They are not revealed unless their Stealth check is beaten by an enemy's Passive Perception or an active Perception check (usually via the Search action).
  • You do not have to constantly re-Hide unless you have been detected. Hide lasts indefinitely.
  • Attacking does not reveal you, it reveals your location. This is the same as when a Hidden creature makes noise, for example if they knock over a vase you will hear a crash and be able to tell where it came from, but this doesn't let you magically see the Hidden creature. It remains hidden.
  • Crawford's rulings are not RAW, and you do not have to abide by their modifications to RAW. If it is troubling to you that Crawford says you can't attack while using Halfling Nimbleness, then move 5ft to the left/right of the Barbarian instead. It doesn't change the outcome.
  • You do not have to remain out of line of sight to be hidden. "Being seen" doesn't mean "in line of sight", it means that the enemy can clearly see you. Darkness, fog, being 1000ft away, are all things that enable you to Hide in line of sight. Once you are Hidden, only an Active Perception check beating your Stealth check will reveal you. You can also stop being Hidden by choice.
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  • 2
    \$\begingroup\$ The rules for Stealth say "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/" It's not correct that you can only be revealed by an active Perception check or by choice. There's a lot of DM's leeway on whether this is going to work — does step one of your play-by-play where you move into the barbarian's square count as "coming out of hiding and approaching the creature"? Arguably so. \$\endgroup\$ – mattdm Nov 15 at 2:39
  • \$\begingroup\$ @mattdm Please reread the quote "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" it continues "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.". It's up to your DM whether or not stepping into the Barbarian's square is "hidden enough" and whether the Boss is able to detect you quickly enough to react. Note that a 5ft step takes a fraction of a second. \$\endgroup\$ – jgn Nov 15 at 2:48
  • \$\begingroup\$ In the midst of combat, someone who you could not previously see jumps out and attacks you. Can you really say you are able to defend yourself as well as if someone who you could see swung a sword at you from plain sight? \$\endgroup\$ – jgn Nov 15 at 2:50
  • \$\begingroup\$ Yep, like I said: a lot of DM's leeway. \$\endgroup\$ – mattdm Nov 15 at 3:10
  • \$\begingroup\$ @mattdm It is up to the DM either way. The rules give no hard answers only "most" "usually" "however" "certain circumstances". This isn't a question of DM leeway, it requires a DM ruling. You seem to be saying that you would rule that as soon as the Rogue enters the Barbarian's square you would say they have been detected. That is a ruling, that is not the rules. \$\endgroup\$ – jgn Nov 15 at 3:24

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